U.S. patent application number 10/220450 was filed with the patent office on 2003-12-11 for insecticidal anthranilamides.
Invention is credited to Lahm, George P., Myers, Brian J., Selby, Thomas P., Stevenson, Thomas M..
Application Number | 20030229050 10/220450 |
Document ID | / |
Family ID | 27497883 |
Filed Date | 2003-12-11 |
United States Patent
Application |
20030229050 |
Kind Code |
A1 |
Lahm, George P. ; et
al. |
December 11, 2003 |
Insecticidal anthranilamides
Abstract
This invention provides compounds of Formula (1), their N-oxides
and agriculturally suitable salts wherein A, B, J, R.sup.1,
R.sup.2, R.sup.3 and R.sup.4 and n are as defined in the
disclosure. Also disclosed are methods for controlling arthropods
comprising contacting the arthropods or their environment with an
arthropodicidally effective amount of a compound of Formula (1) and
compositions containing the compounds of Formula (1).
Inventors: |
Lahm, George P.;
(Wilmington, DE) ; Myers, Brian J.; (Oxford,
PA) ; Selby, Thomas P.; (Wilmington, DE) ;
Stevenson, Thomas M.; (Newark, DE) |
Correspondence
Address: |
Linda D Birch
E I du Pont de Nemours & Company
Legal Patents
Wilmington
DE
19898
US
|
Family ID: |
27497883 |
Appl. No.: |
10/220450 |
Filed: |
August 28, 2002 |
PCT Filed: |
March 20, 2001 |
PCT NO: |
PCT/US01/09338 |
Current U.S.
Class: |
514/63 ; 514/354;
514/423; 514/521; 514/599; 514/616 |
Current CPC
Class: |
A01N 43/08 20130101;
A01N 43/647 20130101; C07D 333/38 20130101; A01N 43/653 20130101;
C07D 277/56 20130101; A01N 37/22 20130101; A01N 43/50 20130101;
C07C 237/44 20130101; C07D 295/192 20130101; A01N 43/10 20130101;
A01N 43/84 20130101; C07C 255/29 20130101; C07D 231/12 20130101;
A01N 37/46 20130101; A01N 43/36 20130101; A01N 43/56 20130101; C07D
401/04 20130101; C07C 317/44 20130101; C07C 2601/02 20170501; C07D
231/06 20130101; C07D 213/82 20130101; A01N 43/42 20130101; C07C
237/42 20130101; C07D 233/90 20130101; C07D 235/08 20130101; C07C
323/42 20130101; A01N 43/90 20130101; C07C 323/62 20130101; A01N
47/02 20130101; C07C 2601/04 20170501; A01N 43/76 20130101; C07D
403/04 20130101; A01N 43/40 20130101; C07C 317/28 20130101; C07D
239/28 20130101; C07D 249/08 20130101; A01N 43/54 20130101; C07C
255/57 20130101; A01N 43/80 20130101; C07D 213/81 20130101; C07D
231/14 20130101; C07D 275/03 20130101; A01N 43/78 20130101 |
Class at
Publication: |
514/63 ; 514/599;
514/616; 514/521; 514/423; 514/354 |
International
Class: |
A01N 055/00; A01N
043/40; A01N 043/36; A01N 037/34; A01N 037/18 |
Claims
What is claimed is:
1. A method for controlling arthropods comprising contacting the
arthropods or their environment with an arthropodicidally effective
amount of a compound of Formula 1, its N-oxide or agriculturally
suitable salts 80wherein A and B are independently O or S; each J
is independently a phenyl or naphthyl group substituted with 1 to 2
R.sup.5 and optionally substituted with 1 to 3 R.sup.6; or each J
is independently a 5- or 6-membered heteroaromatic ring or an
aromatic 8-, 9- or 10-membered fused heterobicyclic ring system
wherein each ring or ring system is optionally substituted with 1
to 4 R.sup.7; n is 1 to 4; R.sup.1 is H; or C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.6
cycloalkyl each optionally substituted with one or more
substituents selected from the group consisting of halogen, CN,
NO.sub.2, hydroxy, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.2-C.sub.4 alkoxycarbonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino and C.sub.3-C.sub.6
cycloalkylamino; or R.sup.1 is C.sub.2-C.sub.6 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl or C(.dbd.A)J; R.sup.2 is H,
C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6
alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 alkoxy,
C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8 dialkylamino,
C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6 alkoxycarbonyl or
C.sub.2-C.sub.6 alkylcarbonyl; R.sup.3 is H; G; C.sub.1-C.sub.6
alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl,
C.sub.3-C.sub.6 cycloalkyl, each optionally substituted with one or
more substituents selected from the group consisting of halogen, G,
CN, NO.sub.2, hydroxy, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.2-C.sub.6
alkoxycarbonyl, C.sub.2-C.sub.6 alcylcarbonyl, C.sub.3-C.sub.6
trialklsilyl, or a phenyl, phenoxy or 5- or 6-membered
heteroaromatic ring, each ring optionally substituted with one to
three substituents independently selected from the group consisting
of C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 haloalkynyl,
C.sub.3-C.sub.6 halocycloalkyl, halogen, CN, NO.sub.2,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.3-C.sub.6
(alkyl)cycloalkylamino, C.sub.2-C.sub.4 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl or C.sub.3-C.sub.6
trialkylsilyl; C.sub.1-C.sub.4 alkoxy; C.sub.1-C.sub.4 alkylamino;
C.sub.2-C.sub.8 dialkylamino; C.sub.3-C.sub.6 cycloalkylamino;
C.sub.2-C.sub.6 alkoxycarbonyl or C.sub.2-C.sub.6 alkylcarbonyl; or
R.sup.2 and R.sup.3 can be taken together with the nitrogen to
which they are attached to form a ring containing 2 to 6 atoms of
carbon and optionally one additional atom of nitrogen, sulfur or
oxygen, said ring may be optionally substituted with 1 to 4
substituents selected from the group consisting of C.sub.1-C.sub.2
alkyl, halogen, CN, NO.sub.2 and C.sub.1-C.sub.2 alkoxy; G is a 5-
or 6-membered nonaromatic carbocyclic or heterocyclic ring,
optionally including one or two ring members selected from the
group consisting of C(.dbd.O), SO or S(O).sub.2 and optionally
substituted with 1 to 4 substituents selected from the group
consisting of C.sub.1-C.sub.2 alkyl, halogen, CN, NO.sub.2 and
C.sub.1-C.sub.2 alkoxy; each R.sup.4 is independently H,
C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6
alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.6 haloalkyl,
C.sub.2-C.sub.6 haloalkenyl, C.sub.2-C.sub.6 haloalkynyl,
C.sub.3-C.sub.6 halocycloalkyl, halogen, CN, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4
haloalkylsulfinyl, C.sub.1-C.sub.4 haloalkylsulfonyl,
C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8 dialkylamino,
C.sub.3-C.sub.6 cycloalkylamino, or C.sub.3-C.sub.6 trialkylsilyl;
or each R.sup.4 is independently phenyl, benzyl or phenoxy, each
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl; each R.sup.5
is independently C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl,
C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.6 haloalkyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, CO.sub.2H, CONH.sub.2, NO.sub.2, hydroxy,
C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.1-C.sub.6
alkylthio, C.sub.1-C.sub.6 alkylsulfinyl, C.sub.1-C.sub.6
alkylsulfonyl, C.sub.1-C.sub.6 haloalkylthio, C.sub.1-C.sub.6
haloalkylsulfinyl, C.sub.l-C.sub.6 haloalkylsulfonyl,
C.sub.1-C.sub.6 alkylamino, C.sub.2-C.sub.12 dialkylamino, or
C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl, C.sub.3-C.sub.6
trialkylsilyl; or (R.sup.5).sub.2 when attached to adjacent carbon
atoms can be taken together as --OCF.sub.2O--,
--CF.sub.2CF.sub.2O--, or --OCF.sub.2CF.sub.2O--; each R.sup.6 is
independently H, halogen, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 alkoxy or C.sub.2-C.sub.4 alkoxycarbonyl; or each
R.sup.6 is independently a phenyl, benzyl, phenoxy, 5- or
6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered
fused heterobicyclic ring system, each ring optionally substituted
with one to three substituents independently selected from the
group consisting of C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl; each R.sup.7
is independently H, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl,
C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.6 haloalkyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, CO.sub.2H, CONH.sub.2, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4
haloalkylsulfinyl, C.sub.1-C.sub.4 haloalkylsulfonyl,
C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8 dialkylamino,
C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl, C.sub.3-C.sub.6
trialkylsilyl; or each R.sup.7 is independently a phenyl, benzyl,
benzoyl, phenoxy, 5- or 6-membered heteroaromatic ring or an
aromatic 8-, 9- or 10-membered fused heterobicyclic ring system,
each ring optionally substituted with one to three substituents
independently selected from the group consisting of C.sub.1-C.sub.4
alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 haloalkynyl,
C.sub.3-C.sub.6 halocycloalkyl, halogen, CN, NO.sub.2,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.3-C.sub.6
(alkyl)cycloalkylamino, C.sub.2-C.sub.4 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl or C.sub.3-C.sub.6
trialkylsilyl; provided that (1) when A and B are both O, R.sup.2
is H or C.sub.1-C.sub.3 alkyl, R.sup.3 is H or C.sub.1-C.sub.3
alkyl and R.sup.4 is H, halogen, C.sub.1-C.sub.6 alkyl, phenyl,
hydroxy or C.sub.1-C.sub.6 alkoxy, then one R.sup.5 is other than
halogen, C.sub.1-C.sub.6 alkyl, hydroxy or C.sub.1-C.sub.6 alkoxy;
or (2) J is other than an optionally substituted
1,2,3-thiadiazole.
2. The method of claim 1 wherein J is a phenyl group substituted
with 1 to 2 R.sup.5 and optionally substituted with 1 to 3
R.sup.6.
3. The method of claim 2 wherein A and B are both O; n is 1 to 2;
R.sup.1 is H, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.2-C.sub.6 alkylcarbonyl or C.sub.2-C.sub.6 alkoxycarbonyl;
R.sup.2 is H, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.2-C.sub.6 alkylcarbonyl or C.sub.2-C.sub.6 alkoxycarbonyl;
R.sup.3 is C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl,
C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.6 cycloalkyl each
optionally substituted with one or more substituents selected from
the group consisting of halogen, CN, C.sub.1-C.sub.2 alkoxy,
C.sub.1-C.sub.2 alkylthio, C.sub.1-C.sub.2 alkylsulfinyl and
C.sub.1-C.sub.2 alkylsulfonyl; one of the R.sup.4 groups is
attached to the phenyl ring at the 2-position or 5-position, and
said R.sup.4 is C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
haloalkylthio, C.sub.1-C.sub.4 haloalkylsulfinyl, C.sub.1-C.sub.4
haloalkylsulfonyl; each R.sup.5 is independently C.sub.1-C.sub.4
haloalkyl, CN, NO.sub.2, C.sub.1-C.sub.4 haloalkoxy,
C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4 alkylsulfinyl,
C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio,
C.sub.1-C.sub.4 haloallylsulfinyl, C.sub.1-C.sub.4
haloalkylsulfonyl or C.sub.2-C.sub.4 alkoxycarbonyl; or
(R.sup.5).sub.2 when attached to adjacent carbon atoms can be taken
together as --OCF.sub.2O--, --CF.sub.2CF.sub.2O-- or
--OCF.sub.2CF.sub.2O--; and each R.sup.6 is independently H,
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.2 alkoxy or
C.sub.2-C.sub.4 alkoxycarbonyl, or each R.sup.6 is independently a
phenyl or a 5- or 6-membered heteroaromatic ring, each ring
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalknyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl.
4. The method of claim 3 wherein R.sup.1 and R.sup.2 are both H;
R.sup.3 is C.sub.1-C.sub.4 alkyl optionally substituted with
halogen, CN, OCH.sub.3, S(O).sub.pCH.sub.3; each R.sup.4 is
independently H, CH.sub.3, CF.sub.3, OCF.sub.3, OCHF.sub.2,
S(O).sub.pCF.sub.3, S(O).sub.pCHF.sub.2, CN or halogen; each
R.sup.5 is independently CF.sub.3, OCF.sub.3, OCHF.sub.2,
S(O).sub.pCF.sub.3, S(O).sub.pCHF.sub.2, OCH.sub.2CF.sub.3,
OCF.sub.2CHF.sub.2, S(O).sub.pCH.sub.2CF.sub.3 or
S(O).sub.pCF.sub.2CHF.s- ub.2; each R.sup.6 is independently H,
halogen or methyl; or phenyl, pyrazole, imidazole; triazole,
pyridine or pyrimidine, each ring optionally substituted with
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, halogen or CN;
and p is 0, 1 or 2.
5. The method of claim 4 wherein R.sup.3 is i-propyl or
t-butyl.
6. The method of claim 1 wherein J is a 5- or 6-membered
heteroaromatic ring optionally substituted with 1 to 4 R.sup.7.
7. The method of claim 6 wherein J is a 5- or 6-membered
heteroaromatic ring selected from the group consisting of J-1, J-2,
J-3, J-4 and J-5, each J optionally substituted with 1 to 3 R.sup.7
81Q is O, S or NR.sup.7; and W, X, Y and Z are independently N or
CR.sup.7, provided that in J-4 and J-5 at least one of W, X, Y or Z
is N.
8. The method of claim 6 or 7 wherein A and B are O; n is 1 to 2;
R.sup.1 is H, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.2-C.sub.6 alkylcarbonyl or
C.sub.2-C.sub.6 alkoxycarbonyl; R.sup.2 is H, C.sub.1-C.sub.4
alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.3-C.sub.6 cycloalkyl, C.sub.2-.sub.6 alkylcarbonyl or
C.sub.2-C.sub.6 alkoxycarbonyl; R.sup.3 is H; or C.sub.1-C.sub.6
alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl or
C.sub.3-C.sub.6 cycloalkyl each optionally substituted with one or
more substituents selected from the group consisting of halogen,
CN, C.sub.1-C.sub.2 alkoxy, C.sub.1-C.sub.2 alkylthio,
C.sub.1-C.sub.2 alkylsulfinyl and C.sub.1-C.sub.2 alkylsulfonyl;
one of the R.sup.4 groups is attached to the phenyl ring at the
2-position, and said R.sup.4 is C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, halogen, CN, NO.sub.2, C.sub.1-C.sub.4
alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4 alkylthio,
C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl,
C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4 haloalkylsulfinyl or
C.sub.1-C.sub.4 haloalkylsulfonyl; and each R.sup.7 is
independently H, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4
haloalkylsulfinyl, C.sub.1-C.sub.4 haloalkylsulfonyl or
C.sub.2-C.sub.4 alkoxycarbonyl; or a phenyl or a 5- or 6-membered
heteroaromatic ring, each ring optionally substituted with
C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 haloalkynyl,
C.sub.3-C.sub.6 halocycloalkyl, halogen, CN, NO.sub.2,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.3-C.sub.6
(alkyl)cycloalkylamino, C.sub.2-C.sub.4 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl or C.sub.3-C.sub.6
trialkylsilyl.
9. The method of claim 8 wherein J is selected from the group
consisting of pyridine, pyrimidine, pyrazole, imidazole, triazole,
thiophene, thiazole and oxazole, furan, isothiazole and isoxazole,
each optionally substituted with 1 to 3 R.sup.7.
10. The method of claim 9 wherein J is selected from the group
consisting of pyridine, pyrimidine, pyrazole, thiophene and
thiazole, each optionally substituted with 1 to 3 R.sup.7; R.sup.1
and R.sup.2 are both H; R.sup.3 is C.sub.1-C.sub.4 alkyl optionally
substituted with halogen, CN, OCH.sub.3, S(O).sub.pCH.sub.3; each
R.sup.4 is independently H, CH.sub.3, CF.sub.3, OCF.sub.3,
OCHF.sub.2, S(O).sub.pCF.sub.3, S(O).sub.pCHF.sub.2, CN or halogen;
each R.sup.7 is independently H, halogen, CH.sub.3, CF.sub.3,
OCHF.sub.2, S(O).sub.pCF.sub.3, S(O).sub.pCHF.sub.2,
OCH.sub.2CF.sub.3, OCF.sub.2CHF.sub.2, S(O).sub.pCH.sub.2CF.sub.3,
S(O).sub.pCF.sub.2CHF.sub.2; or phenyl, pyrazole, imidazole,
triazole, pyridine or pyrimidine, each ring optionally substituted
with C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, halogen or CN; and p is 0, 1 or 2.
11. The method of claim 10 wherein J is a pyridine optionally
substituted with 1 to 3 R.sup.7.
12. The method of claim 11 wherein one R.sup.7 is a phenyl
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, halogen or CN.
13. The method of claim 11 wherein one R.sup.7 is a pyrazole,
imidazole, triazole, pyridine or pyrimidine, each ring optionally
substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
halogen or CN.
14. The method of claim 10 wherein J is a pyrimidine optionally
substituted with 1 to 3 R.sup.7.
15. The method of claim 14 wherein one R.sup.7 is a phenyl
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, halogen or CN.
16. The method of claim 14 wherein one R.sup.7 is a pyrazole,
imidazole, triazole, pyridine or pyrimidine, each ring optionally
substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
halogen or CN.
17. The method of claim 10 wherein J is a pyrazole optionally
substituted with 1 to 3 R.sup.7.
18. The method of claim 17 wherein one R.sup.7 is a phenyl
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, halogen or CN.
19. The method of claim 17 wherein one R.sup.7 is a pyrazole,
imidazole, triazole, pyridine or pyrimidine, each ring optionally
substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
halogen or CN.
20. The method of claim 19 wherein R.sup.7 is a pyridine optionally
substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
halogen or CN.
21. The method of claim 1 comprising a compound of Formula 1
selected from the group consisting of:
3-methyl-N-(1-methylethyl)-2-[[4-(trifluoromethy-
l)benzoyl]amino]-benzamide,
2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]-
carbonyl]phenyl]-4-(trifluoromethyl)benzamide,
2-methyl-N-[2-methyl-6-[[(1-
-methylethyl)amino]carbonyl]phenyl]-6-(trifluoromethyl)-3-pyridinecarboxam-
ide,
1-ethyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trif-
luoromethyl)-1H-pyrazole-5-carboxamide,
1-(2-fluorophenyl)-N-[2-methyl-6-[-
[(1-methylethyl)amino)carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-c-
arboxamide,
1-(3-chloro-2-pyridinyl)-N-[2-methyl-6-[[(1-methylethyl)amino]-
carbonyl]phenyl]3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,
N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyrid-
inyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,
3-bromo-1-(2-chlorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]-
phenyl]-1H-pyrazole-5-carboxamide, and
3-bromo-N-[2-chloro-6-[[(1-methylet-
hyl)amino]carbonyl]phenyl]-1-(2-chlorophenyl)-1H-pyrazole-5-carboxamide.
22. A compound of Formula 1, its N-oxides and agriculturally
suitable salts 82wherein A and B are independently O or S;
optionally substituted with 1 to 3 R.sup.6; or each J is
independently a 5- or 6-membered heteroaromatic ring or an aromatic
8-, 9- or 10-membered fused heterobicyclic ring system wherein each
ring or ring system is optionally substituted with 1 to 4 R.sup.7;
n is 1 to 4; R.sup.1 is H; or C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.6
cycloalkyl each optionally substituted with one or more
substituents selected from the group consisting of halogen, CN,
NO.sub.2, hydroxy, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.2-C.sub.4 alkoxycarbonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino and C.sub.3-C.sub.6
cycloalkylamino; or R.sup.1 is C.sub.2-C.sub.6 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl or C(.dbd.A)J; R.sup.2 is H,
C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6
alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 alkoxy,
C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8 dialkylamino,
C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6 alkoxycarbonyl or
C.sub.2-C.sub.6 alkylcarbonyl; R.sup.3 is H; C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6
cycloalkyl, each optionally substituted with one or more
substituents selected from the group consisting of halogen, CN,
NO.sub.2, hydroxy, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.2-C.sub.6
akoxycarbonyl, C.sub.2-C.sub.6 alkylcarbonyl, C.sub.3-C.sub.6
trialkylsilyl, or a phenoxy ring optionally substituted with one to
three substituents independently selected from the group consisting
of C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 haloalkynyl,
C.sub.3-C.sub.6 halocycloalkyl, halogen, CN, NO.sub.2,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.3-C.sub.6
(alkyl)cycloalkylamino, C.sub.2-C.sub.4 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl or C.sub.3-C.sub.6
trialkylsilyl; C.sub.1-C.sub.4 alkoxy; C.sub.1-C.sub.4 alkylamino;
C.sub.2-C.sub.8 dialkylamino; C.sub.3-C.sub.6 cycloalkylamino;
C.sub.2-C.sub.6 alkoxycarbonyl or C.sub.2-C.sub.6 alkylcarbonyl; or
R.sup.2 and R.sup.3 can be taken together with the nitrogen to
which they are attached to form a ring containing 2 to 6 atoms of
carbon and optionally one additional atom of nitrogen, sulfur or
oxygen, said ring may be optionally substituted with 1 to 4
substituents selected from the group consisting of C.sub.1-C.sub.2
alkyl, halogen, CN, NO.sub.2 and C.sub.1-C.sub.2 alkoxy; each
R.sup.4 is independently H, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.6 haloalkyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, hydroxy, C.sub.1-C.sub.4 alkoxy,
C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4 alkylthio,
C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl,
C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4 haloalkylsulfinyl,
C.sub.1-C.sub.4 haloalkylsulfonyl, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, or
C.sub.3-C.sub.6 trialkylsilyl; or each R.sup.4 is independently
phenyl, benzyl or phenoxy, each optionally substituted with
C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 haloalkynyl,
C.sub.3-C.sub.6 halocycloalkyl, halogen, CN, NO.sub.2,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.3-C.sub.6
(allyl)cycloalkylamino, C.sub.2-C.sub.4 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl or C.sub.3-C.sub.6
trialkylsilyl; each R.sup.5 is independently C.sub.1-C.sub.6
haloalkyl, C.sub.2-C.sub.6 haloalkenyl, C.sub.2-C.sub.6
haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
haloalkylthio, C.sub.1-C.sub.4 haloalkylsulfinyl, C.sub.1-C.sub.4
haloalkylsulfonyl, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxycarbonyl,
C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8 dialkylamino,
C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
or C.sub.3-C.sub.8 dialkylaminocarbonyl; or (R.sup.5).sub.2
attached to adjacent carbon atoms can be taken together as
--OCF.sub.2O--, --CF.sub.2CF.sub.2O--, or --OCF.sub.2CF.sub.2O--;
each R.sup.6 is independently H, halogen, C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.4 alkoxy or C.sub.2-C.sub.4
alkoxycarbonyl; or each R.sup.6 is independently a phenyl, benzyl,
phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9-
or 10-membered fused heterobicyclic ring system, each ring
optionally substituted with one to three substituents independently
selected from the group consisting of C.sub.1-C.sub.4 alkyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl; each R.sup.7
is independently H, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl,
C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.6 haloalkyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, CO.sub.2H, CONH.sub.2, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.l-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4
haloalkylsulfinyl, C.sub.1-C.sub.4 haloalkylsulfonyl,
C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8 dialkylamino,
C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl, C.sub.3-C.sub.6
trialkylsilyl; or each R.sup.7 is independently a phenyl, benzyl,
benzoyl, phenoxy or 5- or 6-membered heteroaromatic ring 8-, 9- or
10-membered fused heterobicyclic ring system, each ring optionally
substituted with one to three substituents independently selected
from the group consisting of C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 haloalkyl C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (allyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl; provided
that (i) at least one R.sup.4 and at least one R.sup.7 are other
than H; (ii) J is other than an optionally substituted
1,2,3-thiadiazole; (iii) when J is an optionally substituted
pyridine and R.sup.2 is H, R.sup.3 is other than H or CH.sub.3;
(iv) when J is an optionally substituted pyridine, then R.sup.7
cannot be CONH.sub.2, C.sub.2-C.sub.6 alkylaminocarbonyl or
C.sub.3-C.sub.8 dialkylaminocarbonyl; (v) when J is an optionally
substituted pyrazole, tetrazole or pyrimidine, then R.sup.2 and
R.sup.3 cannot both be hydrogen.
23. The compound of claim 22 wherein J is a phenyl group
substituted with 1 to 2 R.sup.5 and optionally substituted with 1
to 3 R.sup.6.
24. The compound of claim 25 wherein A and B are both O; n is 1 to
2; R.sup.1 is H, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.2-C.sub.6 alkylcarbonyl or C.sub.2-C.sub.6 alkoxycarbonyl;
R.sup.2 is H, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.2-C.sub.6 alkylcarbonyl or C.sub.2-C.sub.6 alkoxycarbonyl;
R.sup.3 is C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl,
C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.6 cycloalkyl each
optionally substituted with one or more substituents selected from
the group consisting of halogen, CN, C.sub.1-C.sub.2 alkoxy,
C.sub.1-C.sub.2 alkylthio, C.sub.1-C.sub.2 alkylsulfinyl and
C.sub.1-C.sub.2 alkylsulfonyl; one of the R.sup.4 groups is
attached to the phenyl ring at the 2-position or 5-position, and
said R.sup.4 is C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
haloalkylthio, C.sub.1-C.sub.4 haloalkylsulfinyl or C.sub.1-C.sub.4
haloalkylsulfonyl; each R.sup.5 is independently C.sub.1-C.sub.4
haloalkyl, CN, NO.sub.2, C.sub.1-C.sub.4 haloalkoxy,
C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4 alkylsulfinyl,
C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio,
C.sub.1-C.sub.4 haloalkylsulfinyl, C.sub.1-C.sub.4
haloalkylsulfonyl or C.sub.2-C.sub.4 alkoxycarbonyl; or
(R.sup.5).sub.2 when attached to adjacent carbon atoms can be taken
together as --OCF.sub.2O--, --CF.sub.2CF.sub.2-- or
--OCF.sub.2CF.sub.2--; and each R.sup.6 is independently H,
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.2 alkoxy or
C.sub.2-C.sub.4 alkoxycarbonyl, or each R.sup.6 is independently a
phenyl or a 5- or 6-membered heteroaromatic ring, each ring
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl.
25. The compound of claim 26 wherein R.sup.1 and R.sup.2 arc both
H; R.sup.3 is C.sub.1-C.sub.4 alkyl optionally substituted with
halogen, CN, OCH.sub.3, S(O).sub.pCH.sub.3; each R.sup.4 is
independently H, CH.sub.3, CF.sub.3, OCF.sub.3, OCHF.sub.2,
S(O).sub.pCF.sub.3, S(O).sub.pCHF.sub.2, CN or halogen; each
R.sup.5 is independently CF.sub.3, OCF.sub.3, OCHF.sub.2,
S(O).sub.pCF.sub.3, S(O).sub.pCHF.sub.2, OCH.sub.2CF.sub.3,
OCF.sub.2CHF.sub.2, S(O).sub.pCH.sub.2CF.sub.3 or
S(O).sub.pCF.sub.2CHF.s- ub.2; each R.sup.6 is independently H,
halogen or methyl; or phenyl, pyrazole, imidazole, triazole,
pyridine or pyrimidine, each ring optionally substituted with
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, halogen or CN;
and p is 0, 1 or 2.
26. The compound of claim 25 wherein R.sup.3 is i-propyl or
t-butyl.
27. The compound of claim 26 wherein J is a 5- or 6-membered
heteroaromatic ring optionally substituted with 1 to 4 R.sup.7.
28. The compound of claim 27 wherein J is a 5- or 6-membered
heteroaromatic ring selected from the group consisting of J-1, J-2,
J-3, J-4 and J-5, each J optionally substituted with 1 to 3 R.sup.7
83Q is O, S or NR.sup.7; and W, X, Y and Z are independently N or
CR.sup.7, provided that in J-4 and J-5 at least one of W, X, Y or Z
is N.
29. The compound of claim 27 or claim 28 wherein A and B are O; n
is 1 to 2; R.sup.1 is H, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.2-C.sub.6 alkylcarbonyl or
C.sub.2-C.sub.6 alkoxycarbonyl; R.sup.2 is H, C.sub.1-C.sub.4
alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.3-C.sub.6 cycloalkyl, C.sub.2-C.sub.6 alkylcarbonyl or
C.sub.2-C.sub.6 alkoxycarbonyl; R.sup.3 is H; or C.sub.1-C.sub.6
alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl or
C.sub.3-C.sub.6 cycloalkyl each optionally substituted with one or
more substituents selected from the group consisting of halogen,
CN, C.sub.1-C.sub.2 alkoxy, C.sub.1-C.sub.2 alkylthio,
C.sub.1-C.sub.2 alkylsulfinyl and C.sub.1-C.sub.2 alkylsulfonyl;
one of the R.sup.4 groups is attached to the phenyl ring at the
2-position, and said R.sup.4 is C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, halogen, CN, NO.sub.2, C.sub.1-C.sub.4
alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4 alkylthio,
C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl,
C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4 haloalkylsulfinyl or
C.sub.1-C.sub.4 haloalkylsulfonyl; and each R.sup.7 is
independently H, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4
haloalkylsulfinyl, C.sub.1-C.sub.4 haloalkylsulfonyl or
C.sub.2-C.sub.4 alkoxycarbonyl; or a phenyl or a 5- or 6-membered
heteroaromatic ring, each ring optionally substituted with
C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 haloalkynyl,
C.sub.3-C.sub.6 halocycloalkyl, halogen, CN, NO.sub.2,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.3-C.sub.6
(alkyl)cycloalkylamino, C.sub.2-C.sub.4 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl or C.sub.3-C.sub.6
trialkylsilyl.
30. The compound of claim 29 wherein J is selected from the group
consisting of pyridine, pyrimidine, pyrazole, imidazole, triazole,
thiophene, thiazole and oxazole, furan, isothiazole and isoxazole,
each optionally substituted with 1 to 3 R.sup.7.
31. The compound of claim 30 wherein J is selected from the group
consisting of pyridine, pyrimidine, pyrazole, thiophene and
thiazole, each optionally substituted with 1 to 3 R.sup.7; R.sup.1
and R.sup.2 are both H; R.sup.3 is C.sub.1-C.sub.4 alkyl optionally
substituted with halogen, CN, OCH.sub.3, S(O).sub.pCH.sub.3; each
R.sup.4 is independently H, CH.sub.3, CF.sub.3, OCF.sub.3,
OCHF.sub.2, S(O).sub.pCF.sub.3, S(O).sub.pCHF.sub.2, CN or halogen;
each R.sup.7 is independently H, halogen, CH.sub.3, CF.sub.3,
OCHF.sub.2, S(O).sub.pCF.sub.3, S(O).sub.pCHF.sub.2,
OCH.sub.2CF.sub.3, OCF.sub.2CHF.sub.2, S(O).sub.pCH.sub.2CF.sub.3,
S(O).sub.pCF.sub.2CHF.sub.2; or phenyl, pyrazole, imidazole,
triazole, pyridine or pyrimidine, each ring optionally substituted
with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, halogen or CN; and p is 0, 1 or 2.
32. The compound of claim 31 wherein J is a pyridine optionally
substituted with 1 to 3R.sup.7.
33. The compound of claim 32 wherein one R.sup.7 is a phenyl
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, halogen or CN.
34. The compound of claim 32 wherein one R.sup.7 is a pyrazole,
imidazole, triazole, pyridine or pyrimidine, each ring optionally
substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
halogen or CN.
35. The compound of claim 31 wherein J is a pyrimidine optionally
substituted with 1 to 3 R.sup.7.
36. The compound of claim 35 wherein one R.sup.7 is a phenyl
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, halogen or CN.
37. The compound of claim 35 wherein one R.sup.7 is a pyrazole,
imidazole, triazole, pyridine or pyrimidine, each ring optionally
substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
halogen or CN.
38. The compound of claim 32 wherein J is a pyrazole optionally
substituted with 1 to 3 R.sup.7.
39. The compound of claim 38 wherein one R.sup.7 is a phenyl
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, halogen or CN.
40. The compound of claim 38 wherein one R.sup.7 is a pyrazole,
imidazole, triazole, pyridine or pyrimidine, each ring optionally
substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalknyl,
halogen or CN.
41. The compound of claim 38 wherein wherein R.sup.7 is a pyridine
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, halogen or CN.
42. The compound of claim 22 selected from the group consisting of:
3-methyl-N-(1-methylethyl)-2-[[4-(trifluoromethyl)benzoyl]amino]-benzamid-
e,
2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-4-(trifl-
uoromethyl)benzamide,
2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbon-
yl]phenyl]-6-(trifluoromethyl)-3-pyridinecarboxamide,
1-ethyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluor-
omethyl)-1H-pyrazole-5-carboxamide,
1-(2-fluorophenyl)-N-[2-methyl-6-[[(1--
methylethyl)amino)carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carbo-
xamide, b
1-(3-chloro-2-pyridinyl)-N-[2-methyl-6-[[(1-methylethyl)amino]ca-
rbonyl]phenyl]3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,
N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyrid-
inyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,
3-bromo-1-(2-chlorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]-
phenyl]-1H-pyrazole-5-carboxamide, and
3-bromo-N-[2-chloro-6-[[(1-methylet-
hyl)amino]carbonyl]phenyl]-1-(2-chlorophenyl)-1H-pyrazole-5-carboxamide.
43. An arthropodicidal composition comprising an arthropodicidally
effective amount of a compound of Formula 1 as described in claim 1
and at least one additional component selected from the group
consisting of surfactants, solid diluents and liquid diluents.
Description
BACKGROUND OF THE INVENTION
[0001] This invention relates to certain anthranilamides, their
N-oxides, agriculturally suitable salts and compositions, and
methods of their use as arthropodicides in both agronomic and
nonagronomic environments.
[0002] The control of arthropod pests is extremely important in
achieving high crop efficiency. Arthropod damage to growing and
stored agronomic crops can cause significant reduction in
productivity and thereby result in increased costs to the consumer.
The control of arthropod pests in forestry, greenhouse crops,
ornamentals, nursery crops, stored food and fiber products,
livestock, household, and public and animal health is also
important. Many products are commercially available for these
purposes, but the need continues for new compounds that are more
effective, less costly, less toxic, environmentally safer or have
different modes of action.
[0003] NL 9202078 discloses N-acyl anthranilic acid derivatives of
Formula i as insecticides 1
[0004] wherein, inter alia,
[0005] X is a direct bond;
[0006] Y is H or C.sub.1-C.sub.6 alkyl;
[0007] Z is NH.sub.2, NH(C.sub.1-C.sub.3 alkyl) or
N(C.sub.1-C.sub.3 alkyl).sub.2; and
[0008] R.sup.1 through R.sup.9 are independently H, halogen,
C.sub.1-C.sub.6 alkyl, phenyl, hydroxy, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.7 acyloxy.
SUMMARY OF THE INVENTION
[0009] This invention pertains to a method for controlling
arthropods comprising contacting the arthropods or their
environment with an arthropodicidally effective amount of a
compound of Formula 1, its N-oxide or agriculturally suitable salts
2
[0010] wherein
[0011] A and B are independently O or S;
[0012] each J is independently a phenyl or naphthyl group
substituted with 1 to 2 R.sup.5 and optionally substituted with 1
to 3 R.sup.6;
[0013] or each J is independently a 5- or 6-membered heteroaromatic
ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring
system wherein each ring or ring system is optionally substituted
with 1 to 4 R.sup.7;
[0014] n is 1 to 4;
[0015] R.sup.1 is H; or C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 akynyl or C.sub.3-C.sub.6 cycloalkyl each
optionally substituted with one or more substituents selected from
the group consisting of halogen, CN, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.2-C.sub.4
alkoxycarbonyl, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino and C.sub.3-C.sub.6 cycloalkylamino; or
[0016] R.sup.1 is C.sub.2-C.sub.6 alkylcarbonyl, C.sub.2-C.sub.6
alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C(.dbd.A)J;
[0017] R.sup.2 is H, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6
alkoxycarbonyl or C.sub.2-C.sub.6 alkylcarbonyl;
[0018] R.sup.3 is H; G; C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl, each
optionally substituted with one or more substituents selected from
the group consisting of halogen, G, CN, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6
alkylcarbonyl, C.sub.3-C.sub.6 trialkylsilyl, or a phenyl, phenoxy
or 5- or 6-membered heteroaromatic ring, each ring optionally
substituted with one to three substituents independently selected
from the group consisting of C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl;
C.sub.1-C.sub.4 alkoxy; C.sub.1-C.sub.4 alkylamino; C.sub.2-C.sub.8
dialkylamino; C.sub.3-C.sub.6 cycloalkylamino; C.sub.2-C.sub.6
alkoxycarbonyl or C.sub.2-C.sub.6 alkylcarbonyl; or
[0019] R.sup.2 and R.sup.3 can be taken together with the nitrogen
to which they are attached to form a ring containing 2 to 6 atoms
of carbon and optionally one additional atom of nitrogen, sulfur or
oxygen, said ring may be optionally substituted with 1 to 4
substituents selected from the group consisting of C.sub.1-C.sub.2
alkyl, halogen, CN, NO.sub.2 and C.sub.1-C.sub.2 alkoxy;
[0020] G is a 5- or 6-membered nonaromatic carbocyclic or
heterocyclic ring, optionally including one or two ring members
selected from the group consisting of C(.dbd.O), SO or S(O).sub.2
and optionally substituted with 1 to 4 substituents selected from
the group consisting of C.sub.1-C.sub.2 alkyl, halogen, CN,
NO.sub.2 and C.sub.1-C.sub.2 alkoxy;
[0021] each R.sup.4 is independently H, C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, hydroxy, C.sub.1-C.sub.4 alkoxy,
C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4 alkylthio,
C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl,
C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4 haloalkylsulfinyl,
C.sub.1-C.sub.4 haloalkylsulfonyl, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, or
C.sub.3-C.sub.6 trialkylsilyl; or
[0022] each R.sup.4 is independently phenyl, benzyl or phenoxy,
each optionally substituted with C.sub.1-C.sub.4 alkyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl;
[0023] each R.sup.5 is independently C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, CO.sub.2H, CONH.sub.2, NO.sub.2, hydroxy,
C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.1-C.sub.6
alkylthio, C.sub.1-C.sub.6 alkylsulfinyl, C.sub.1-C.sub.6
alkylsulfonyl, C.sub.1-C.sub.6 haloalkylthio, C.sub.1-C.sub.6
haloalkylsulfinyl, C.sub.1-C.sub.6 haloalkylsulfonyl,
C.sub.1-C.sub.6 alkylamino, C.sub.2-C.sub.12 dialkylamino, or
C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl, C.sub.3-C.sub.6
trialkylsilyl; or
[0024] (R.sup.5).sub.2 when attached to adjacent carbon atoms can
be taken together as --OCF.sub.2O--, --CF.sub.2CF.sub.2O--, or
--OCF.sub.2CF.sub.2O--;
[0025] each R.sup.6 is independently H, halogen, C.sub.1-C.sub.6
alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl,
C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 alkoxy or
C.sub.2-C.sub.4 alkoxycarbonyl; or
[0026] each R.sup.6 is independently a phenyl, benzyl, phenoxy, 5-
or 6-membered heteroaromatic ring or an aromatic 8-, 9- or
10-membered fused heterobicyclic ring system, each ring optionally
substituted with one to three substituents independently selected
from the group consisting of C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl;
[0027] each R.sup.7 is independently H, C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, CO.sub.2H, CONH.sub.2, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4
haloalkylsulfinyl, C.sub.1-C.sub.4 haloalkylsulfonyl,
C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8 dialkylamino,
C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl, C.sub.3-C.sub.6
trialkylsilyl; or
[0028] each R.sup.7 is independently a phenyl, benzyl, benzoyl,
phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9-
or 10-membered fused heterobicyclic ring system, each ring
optionally substituted with one to three substituents independently
selected from the group consisting of C.sub.1-C.sub.4 alkyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl;
[0029] provided that
[0030] (1) when A and B are both O, R.sup.2 is H or C.sub.1-C.sub.3
alkyl, R.sup.3 is H or C.sub.1-C.sub.3 alkyl and R.sup.4 is H,
halogen, C.sub.1-C.sub.6 alkyl, phenyl, hydroxy or C.sub.1-C.sub.6
alkoxy, then one R.sup.5 is other than halogen, C.sub.1-C.sub.6
alkyl, hydroxy or C.sub.1-C.sub.6 alkoxy; or
[0031] (2) J is other than an optionally substituted
1,2,3-thiadiazole.
[0032] This invention also pertains to compounds of Formula 1,
their N-oxides and. agriculturally suitable salts 3
[0033] wherein
[0034] A and B are independently O or S;
[0035] each J is independently a phenyl or naphthyl group
substituted with 1 to 2 R.sup.5 and optionally substituted with 1
to 3 R.sup.6;
[0036] or each J is independently a 5- or 6-membered heteroaromatic
ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring
system wherein each ring or ring system is optionally substituted
with 1 to 4 R.sup.7;
[0037] n is 1 to 4;
[0038] R.sup.1 .sup..sub.H; or C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.6
cycloalkyl each optionally substituted with one or more
substituents selected from the group consisting of halogen, CN,
NO.sub.2, hydroxy, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.2-C.sub.4 alkoxycarbonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino and C.sub.3-C.sub.6
cycloalkylamino; or
[0039] R.sup.1 is C.sub.2-C.sub.6 alkylcarbonyl, C.sub.2-C.sub.6
alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylarinocarbonyl or C(.dbd.A)J;
[0040] R.sup.2 is H, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6
alkoxycarbonyl or C.sub.2-C.sub.6 alkylcarbonyl;
[0041] R.sup.3 is H; C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl, each
optionally substituted with one or more substituents selected from
the group consisting of halogen, CN, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6
alkylcarbonyl, C.sub.3-C.sub.6 trialkylsilyl, or a phenoxy ring
optionally substituted with one to three substituents independently
selected from the group consisting of C.sub.1-C.sub.4 alkyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl;
C.sub.1-C.sub.4 alkoxy; C.sub.1-C.sub.4 alkylamino; C.sub.2-C.sub.8
dialkylamino; C.sub.3-C.sub.6 cycloalkylamino; C.sub.2-C.sub.6
alkoxycarbonyl or C.sub.2-C.sub.6 alkylcarbonyl; or
[0042] R.sup.2 and R.sup.3 can be taken together with the nitrogen
to which they are attached to form a ring containing 2 to 6 atoms
of carbon and optionally one additional atom of nitrogen, sulfur or
oxygen, said ring may be optionally substituted with 1 to 4
substituents selected from the group consisting of C.sub.1-C.sub.2
alkyl, halogen, CN, NO.sub.2 and C.sub.1-C.sub.2 alkoxy;
[0043] each R.sup.4 is independently H, C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, hydroxy, C.sub.1-C.sub.4 alkoxy,
C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4 alkylthio,
C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl,
C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4 haloalkylsulfinyl,
C.sub.1-C.sub.4 haloalkylsulfonyl, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, or
C.sub.3-C.sub.6 trialkylsilyl; or
[0044] each R.sup.4 is independently phenyl, benzyl or phenoxy,
each optionally substituted with C.sub.1-C.sub.4 alkyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl;
[0045] each R.sup.5 is independently C.sub.1-C.sub.6 haloalkyl,
C.sub.2-C.sub.6 haloalkenyl, C.sub.2-C.sub.6 haloalkynyl,
C.sub.3-C.sub.6 halocycloalkyl, C.sub.1-C.sub.4 haloalkoxy,
C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4 alkylsulfinyl,
C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio,
C.sub.1-C.sub.4 haloalkylsulfinyl, C.sub.1-C.sub.4
haloalkylsulfonyl, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxycarbonyl,
C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8 dialkylamino,
C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
or C.sub.3-C.sub.8 dialkylaminocarbonyl; or
[0046] (R.sup.5).sub.2 attached to adjacent carbon atoms can be
taken together as --OCF.sub.2O--, --CF.sub.2CF.sub.2O--, or
--OCF.sub.2CF.sub.2O--;
[0047] each R.sup.6 is independently H, halogen, C.sub.1-C.sub.6
alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl,
C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 alkoxy or
C.sub.2-C.sub.4 alkoxycarbonyl; or
[0048] each R.sup.6 is independently a phenyl, benzyl, phenoxy, 5-
or 6-membered heteroaromatic ring or an aromatic 8-, 9- or
10-membered fused heterobicyclic ring system, each ring optionally
substituted with one to three substituents independently selected
from the group consisting of C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.3-C.sub.6
(alkyl)cycloalkylamino, C.sub.2-C.sub.4 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl or C.sub.3-C.sub.6
trialkylsilyl;
[0049] each R.sup.7 is independently H, C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, CO.sub.2H, CONH.sub.2, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4
haloalkylsulfinyl, C.sub.1-C.sub.4 haloalkylsulfonyl,
C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8 dialkylamino,
C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl, C.sub.3-C.sub.6
trialkylsilyl; or
[0050] each R.sup.7 is independently a phenyl, benzyl, benzoyl,
phenoxy or 5- or 6-membered heteroaromatic ring 8-, 9- or
10-membered fused heterobicyclic ring system, each ring optionally
substituted with one to three substituents independently selected
from the group consisting of C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkyl, C.sub.3-C.sub.6 halocycloalkyl, halogen,
CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy,
C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4 alkylsulfinyl,
C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6 cycloalkylamino,
C.sub.3-C.sub.6 (alkyl)cycloalkylamino, C.sub.2-C.sub.4
alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6
alkylaninocarbonyl, C.sub.3-C.sub.8 dialkylaminocarbonyl or
C.sub.3-C.sub.6 trialkylsilyl;
[0051] provided that
[0052] (i) at least one R.sup.4 and at least one R.sup.7 are other
than H;
[0053] (ii) J is other than an optionally substituted
1,2,3-thiadiazole;
[0054] (iii) when J is an optionally substituted pyridine and
R.sup.2 is H, R.sup.3 is other than H or CH.sub.3;
[0055] (iv) when J is an optionally substituted pyridine, then
R.sup.7 cannot be CONH.sub.2, C.sub.2-C.sub.6 alkylaminocarbonyl or
C.sub.3-C.sub.8 dialkylaminocarbonyl;
[0056] (v) when J is an optionally substituted pyrazole, tetrazole
or pyrimidine, then R.sup.2 and R.sup.3 cannot both be
hydrogen.
[0057] This invention also pertains to arthropodicidal compositions
comprising an arthropodicidally effective amount of a compound of
Formula 1 and at least one additional component selected from the
group consisting of surfactants, solid diluents and liquid
diluents.
DETAILS OF THE INVENTION
[0058] In the above recitations, the term "alkyl", used either
alone or in compound words such as "alkylthio" or "haloalkyl"
includes straight-chain or branched alkyl, such as, methyl, ethyl,
n-propyl, i-propyl, or the different butyl, pentyl or hexyl
isomers. The term "1-2 alkyl" indicates that one or two of the
available positions for that substituent may be alkyl. "Alkenyl"
includes straight-chain or branched alkenes such as 1-propenyl,
2-propenyl, and the different butenyl, pentenyl and hexenyl
isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl
and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched
alkynes such as 1-propynyl, 2-propynyl and the different butynyl,
pentynyl and hexynyl isomers. "Alkynyl" can also include moieties
comprised of multiple triple bonds such as 2,5-hexadiynyl. "Alkoxy"
includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy
and the different butoxy, pentoxy and hexyloxy isomers.
"Alkoxyalkyl" denotes alkoxy substitution on alkyl. Examples of
"alkoxyalkyl" include CH.sub.3OCH.sub.2, CH.sub.3OCH.sub.2CH.sub.2,
CH.sub.3CH.sub.2OCH.sub.2,
CH.sub.3CH.sub.2CH.sub.2CH.sub.2OCH.sub.2 and
CH.sub.3CH.sub.2OCH.sub.2CH- .sub.2. "Alkylthio" includes branched
or straight-chain alkylthio moieties such as methylthio, ethylthio,
and the different propylthio, butylthio, pentylthio and hexylthio
isomers. "Cycloalkyl" includes, for example, cyclopropyl,
cyclobutyl, cyclopentyl and cyclohexyl.
[0059] The term "heterocyclic ring" or heterocyclic ring system"
denotes rings or ring systems in which at least one ring atom is
not carbon and comprises 1 to 4 heteroatoms independently selected
from the group consisting of nitrogen, oxygen and sulfur, provided
that each heterocyclic ring contains no more than 4 nitrogens, no
more than 2 oxygens and no more than 2 sulfurs. The heterocyclic
ring can be attached through any available carbon or nitrogen by
replacement of hydrogen on said carbon or nitrogen. The term
"aromatic ring system" denotes fully unsaturated carbocycles and
heterocycles in which the polycyclic ring system is aromatic (where
aromatic indicates that the Huickel rule is satisfied for the ring
system). The term "heteroaromatic ring" denotes fully aromatic
rings in which at least one ring atom is not carbon and comprises 1
to 4 heteroatoms independently selected from the group consisting
of nitrogen, oxygen and sulfur, provided that each heterocyclic
ring contains no more than 4 nitrogens, no more than 2 oxygens and
no more than 2 sulfurs (where aromatic indicates that the Huickel
rule is satisfied). The heterocyclic ring can be attached through
any available carbon or nitrogen by replacement of hydrogen on said
carbon or nitrogen. The term "aromatic heterocyclic ring system"
includes fully aromatic heterocycles and heterocycles in which at
least one ring of a polycyclic ring system is aromatic (where
aromatic indicates that the Huickel rule is satisfied). The term
"fused heterobicyclic ring system" includes a ring system comprised
of two fused rings in which at least one ring atom is not carbon
and can be aromatic or non aromatic, as defined above.
[0060] The term "halogen", either alone or in compound words such
as "haloalkyl", includes fluorine chlorine bromine or iodine.
Further, when used in compound words such as "haloalkyl", said
alkyl may be partially or fully substituted with halogen atoms
which may be the same or different. Examples of"haloalkyl" include
F.sub.3C, ClCH.sub.2, CF.sub.3CH.sub.2 and CF.sub.3CCl.sub.2. The
terms "haloalkenyl", "haloalkynyl", "haloalkoxy", and the like, are
defined analogously to the term "haloalkyl". Examples of
"haloalkenyl" include (Cl).sub.2C.dbd.CHCH.sub.2 and
CF.sub.3CH.sub.2CH.dbd.CHCH.sub.2. Examples of "haloalkynyl"
include HC.ident.CCHCl, CF.sub.3C.ident.C, CCl.sub.3C.ident.C and
FCH.sub.2C.ident.CCH.sub.2. Examples of "haloalkoxy" include
CF.sub.3O, CCl.sub.3CH.sub.2O, HCF.sub.2CH.sub.2CH.sub.2O and
CF.sub.3CH.sub.2O.
[0061] The total number of carbon atoms in a substituent group is
indicated by the "C.sub.i-C.sub.j" prefix where i and j are numbers
from 1 to 6. For example, C.sub.1-C.sub.3 alkylsulfonyl designates
methylsulfonyl through propylsulfonyl; C.sub.2 alkoxyalkyl
designates CH.sub.3OCH.sub.2; C.sub.3 alkoxyalkyl designates, for
example, CH.sub.3CH(OCH.sub.3), CH.sub.3OCH.sub.2CH.sub.2 or
CH.sub.3CH.sub.2OCH.sub.2; and C.sub.4 alloxyalkyl designates the
various isomers of an alkyl group substituted with an alkoxy group
containing a total of four carbon atoms, examples including
CH.sub.3CH.sub.2CH.sub.2OC- H.sub.2 and
CH.sub.3CH.sub.2OCH.sub.2CH.sub.2. In the above recitations, when a
compound of Formula 1 contains a heterocyclic ring, all
substituents are attached to this ring through any available carbon
or nitrogen by replacement of a hydrogen on said carbon or
nitrogen.
[0062] When a group contains a substituent which can be hydrogen,
for example R.sup.3, then, when this substituent is taken as
hydrogen, it is recognized that this is equivalent to said group
being unsubstituted.
[0063] Compounds of this invention can exist as one or more
stereoisomers. The various stereoisomers include enantiomers,
diastereomers, atropisomers and geometric isomers. One skilled in
the art will appreciate that one stereoisomer may be more active
and/or may exhibit beneficial effects when enriched relative to the
other stercoisomer(s) or when separated from the other
stereoisomer(s). Additionally, the skilled artisan knows how to
separate, enrich, and/or to selectively prepare said stereoisomers.
Accordingly, the compounds of the invention may be present as a
mixture of stereoisomers, individual stereoisomers, or as an
optically active form.
[0064] The present invention comprises compounds selected from
Formula 1, N-oxides and agriculturally suitable salts thereof. One
skilled in the art will appreciate that not all nitrogen containing
heterocycles can form N-oxides since the nitrogen requires an
available lone pair for oxidation to the oxide; one skilled in the
art will recognize those nitrogen containing heterocycles which can
form N-oxides. One skilled in the art will also recognize that
tertiary amines can form N-oxides. Synthetic methods for the
preparation of N-oxides of heterocycles and tertiary amines are
very well known by one skilled in the art including the oxidation
of heterocycles and tertiary amines with peroxy acids such as
peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide,
alkyl hydroperoxides such as t-butyl hydroperoxide, sodium
perborate, and dioxiranes such as dimethydioxirane. These methods
for the preparation of n-oxides have been extensively described and
reviewed in the literature, see for example: T. L. Gilchrist in
Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley,
Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive
Heterocyclic Chemistry, vol. 3, pp 18-19, A. J. Boulton and A.
McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene
in Advances in Heterocyclic Chemistry, vol. 43, pp 139-151, A. R.
Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in
Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R.
Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H.
Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic
Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton,
Eds., Academic Press.
[0065] The salts of the compounds of the invention include
acid-addition salts with inorganic or organic acids such as
hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic,
butyric, fumaric, lactic, maleic, malonic, oxalic, propionic,
salicylic, tartaric, 4-toluenesulfonic or valeric acids.
[0066] Of note are certain compounds of formula II 4
[0067] wherein
[0068] X and Y are O;
[0069] m is 1 to 5;
[0070] n is 1 to 4;
[0071] R.sup.1 .sup..sub.H; or C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.6
cycloalkyl each optionally substituted with one or more
substituents selected from the group consisting of halogen, CN,
NO.sub.2, hydroxy, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.2-C.sub.4 alkoxycarbonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino and C.sub.3-C.sub.6
cycloalkylamino; or
[0072] R.sup.1 is C.sub.2-C.sub.6 alkylcarbonyl, C.sub.2-C.sub.6
alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl or
C.sub.3-C.sub.8 dialkylaminocarbonyl;
[0073] R.sup.2 is H, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 alkoxy C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6
alkoxycarbonyl or C.sub.2-C.sub.6 alkylcarbonyl;
[0074] R.sup.3 is i-propyl or t-butyl; and
[0075] each R.sup.4 and R.sup.5 are independently H,
C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6
alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.6 haloalkyl,
C.sub.2-C.sub.6 haloalkenyl, C.sub.2-C.sub.6 haloalkynyl,
C.sub.3-C.sub.6 halocycloalkyl, halogen, CN, CO.sub.2H, CONH.sub.2,
NO.sub.2, hydroxy, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
haloalkylthio, C.sub.1-C.sub.4 haloalkylsulfinyl, C.sub.1-C.sub.4
haloalkylsulfonyl, C.sub.1-C.sub.4 alkoxycarbonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.2-C.sub.6 alkylcarbonyl, C.sub.2-C.sub.6
alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl, C.sub.3-C.sub.6 trialkylsilyl; or
[0076] each R.sup.4 and R.sup.5 are independently phenyl optionally
substituted with C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 haolalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl C.sub.1-C.sub.4
alkoxycarbonyl, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.3-C.sub.6
(alkyl)cycloalkylamino, C.sub.2-C.sub.4 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl or C.sub.3-C.sub.6
trialkylsilyl.
[0077] Also of note are methods for controlling arthropods
comprising contacting the arthropods or their environment with an
arthropodicidally effective amount of a compound of Formula II and
insecticidal compositions thereof.
[0078] Also of note are certain compounds of Formula III 5
[0079] wherein
[0080] A and B are independently O or S;
[0081] J is a phenyl group substituted with 1 to 2 R.sup.5 and
optionally substituted with 1 to 3 R.sup.6, or a 5- or 6-membered
heteroaromatic ring optionally substituted with 1 to 4 R.sup.7;
[0082] n is 1 to 4;
[0083] R.sup.1 is H; or C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.6 cycloalkyl each
optionally substituted with one or more substituents selected from
the group consisting of halogen, CN, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.2-C.sub.4
alkoxycarbonyl, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino and C.sub.3-C.sub.6 cycloalkylamino; or
[0084] R.sup.1 is C.sub.2-C.sub.6 alkylcarbonyl, C.sub.2-C.sub.6
alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl or
C.sub.3-C.sub.8 dialkylaminocarbonyl;
[0085] R.sup.2 is H, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6
alkoxycarbonyl or C.sub.2-C.sub.6 alkylcarbonyl;
[0086] R.sup.3 is H; or C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.6 cycloalkyl each
optionally substituted with one or more substituents selected from
the group consisting of halogen, CN, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl and C.sub.1-C.sub.4 alkylsulfonyl; or
[0087] R.sup.2 and R.sup.3 can be taken together with the nitrogen
to which they are attached to form a ring containing 2 to 6 atoms
of carbon and optionally one additional atom of nitrogen, sur or
oxygen, said ring may be optionally substituted with 1 to 4
substituents selected from the group consisting of C.sub.1-C.sub.2
alkyl, halogen, CN, NO.sub.2 and C.sub.1-C.sub.2 alkoxy;
[0088] each R.sup.4 is independently H, C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, CO.sub.2H, CONH.sub.2, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4
haloalkylsulfinyl, C.sub.l-C.sub.4 haloalkylsulfonyl,
C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8 dialkylamino,
C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl, C.sub.3-C.sub.6
trialkylsilyl; or
[0089] each R.sup.4 is independently phenyl, benzyl or phenoxy,
each optionally substituted with C.sub.1-C.sub.4 alkyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.4 haolalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl;
[0090] each R.sup.5 is independently C.sub.1-C.sub.6 haloalkyl,
C.sub.2-C.sub.6 haloalkenyl, C.sub.2-C.sub.6 haloalkynyl,
C.sub.3-C.sub.6 halocycloalkyl, C.sub.1-C.sub.4 haloalkoxy,
C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4 alkylsulfinyl,
C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio,
C.sub.1-C.sub.4 haloalkylsulfinyl, C.sub.1-C.sub.4
haloalkylsulfonyl, CN, NO.sub.2, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6 cycloalkylamino,
C.sub.2-C.sub.6 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, or C.sub.3-C.sub.8
dialkylaminocarbonyl; or
[0091] (R.sup.5).sub.2 when attached to adjacent carbon atoms can
be taken together as --OCF.sub.2O--, --CF.sub.2CF.sub.2O--, or
--OCF.sub.2CF.sub.2O--;
[0092] each R.sup.6 is independently H, halogen, C.sub.1-C.sub.6
alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl,
C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 alkoxy; or
[0093] each R.sup.6 is independently phenyl, benzyl or phenoxy,
each optionally substituted with C.sub.1-C.sub.4 alkyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.4 haolalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (aklky)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl;
[0094] each R.sup.7 is independently H, C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, CO.sub.2H, CONH.sub.2, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4
haloalkylsulfinyl, C.sub.1-C.sub.4 haloalkylsulfonyl,
C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8 dialkylamino,
C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl, C.sub.3-C.sub.6
trialkylsilyl; or
[0095] each R.sup.7 is independently phenyl, benzyl or phenoxy,
each optionally substituted with C.sub.1-C.sub.4 alkyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl C.sub.1-C.sub.4
alkoxycarbonyl, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.3-C.sub.6
(alkyl)cycloalkylamino, C.sub.2-C.sub.4 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.3 dialkylaminocarbonyl or C.sub.3-C.sub.6
trialkylsilyl.
[0096] Also of note are methods for controlling arthropods
comprising contacting the arthropods or their environment with an
arthropodicidally effective amount of a compound of Formula III and
insecticidal compositions thereof.
[0097] Also of note are certain compounds of Formula IV 6
[0098] wherein
[0099] A and B are independently O or S;
[0100] J is a phenyl group substituted with 1 to 2 R.sup.5 and
optionally substituted with 1 to 3 R.sup.6, or a 5- or 6-membered
heteroaromatic ring optionally substituted with 1 to 4 R.sup.7;
[0101] n is 1 to 4;
[0102] R.sup.1 is H; or C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.6 cycloalkyl each
optionally substituted with one or more substituents selected from
the group consisting of halogen, CN, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.2-C.sub.4
alkoxycarbonyl, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino and C.sub.3-C.sub.6 cycloalkylamino; or
[0103] R.sup.1 is C.sub.2-C.sub.6 alkylcarbonyl, C.sub.2-C.sub.6
alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl or
C.sub.3-C.sub.8 dialkylaminocarbonyl;
[0104] R.sup.2 is H, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6
alkoxycarbonyl or C.sub.2-C.sub.6 alkylcarbonyl;
[0105] R.sup.3 is H; C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl, each
optionally substituted with one or more substituents selected from
the group consisting of halogen, CN, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl and C.sub.1-C.sub.4 alkylsulfonyl; C.sub.1-C.sub.4
alkoxy; C.sub.1-C.sub.4alkylamino; C.sub.2-C.sub.8 dialkylamino;
C.sub.3-C.sub.6 cycloalkylamino; C.sub.2-C.sub.6 alkoxycarbonyl or
C.sub.2-C.sub.6 alkylcarbonyl; or
[0106] R.sup.2 and R.sup.3 can be taken together with the nitrogen
to which they are attached to form a ring containing 2 to 6 atoms
of carbon and optionally one additional atom of nitrogen sulfur or
oxygen, said ring may be optionally substituted with 1 to 4
substituents selected from the group consisting of C.sub.1-C.sub.2
alkyl, halogen, CN, NO.sub.2 and C.sub.1-C.sub.2 alkoxy;
[0107] each R.sup.4 is independently H, C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, CO.sub.2H, CONH.sub.2, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4
haloalkylsulfinyl, C.sub.1-C.sub.4 haloalkylsulfonyl,
C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8 dialkylamino,
C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl, C.sub.3-C.sub.6
trialkylsilyl; or
[0108] each R.sup.4 is independently phenyl, benzyl or phenoxy,
each optionally substituted with C.sub.1-C.sub.4 alkyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.4 haolalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl;
[0109] each R.sup.5 is independently C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 haloalkynyl, C.sub.3-C.sub.6 halocyloalkyl,
halogen, CN, CO.sub.2H, CONH.sub.2, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4
haloalkylsulfinyl, C.sub.1-C.sub.4 haloalkylsulfonyl,
C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8 dialkylamino,
C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl, C.sub.3-C.sub.6
trialkylsilyl; or
[0110] (R.sup.5).sub.2 when attached to adjacent carbon atoms can
be taken together as --OCF.sub.2O--, --CF.sub.2CF.sub.2O--, or
--OCF.sub.2CF.sub.2O--;
[0111] each R.sup.6 is independently H, halogen, C.sub.1-C.sub.6
alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl,
C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 alkoxy; or
[0112] each R.sup.6 is independently a phenyl, benzyl, phenoxy or a
5- or 6-membered heteroaromatic ring, each ring optionally
substituted with C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl C.sub.2-C.sub.6
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl;
[0113] each R.sup.7 is independently H, C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, CO.sub.2H, CONH.sub.2, NO.sub.2, hydroxy,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4
haloalkylsulfinyl, C.sub.1-C.sub.4 haloalkylsulfonyl,
C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8 dialkylamino,
C.sub.3-C.sub.6 cycloalkylamino, C.sub.2-C.sub.6 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl, C.sub.3-C.sub.6
trialkylsilyl; or
[0114] each R.sup.7 is independently a phenyl, benzyl, benzoyl,
phenoxy or a 5- or 6-membered heteroaromatic ring, each ring
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 haolalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl;
[0115] provided that when A and B are both O, R.sup.2 is H or
C.sub.1-C.sub.3 alkyl, R.sup.3 is H or C.sub.1-C.sub.3 alkyl and
R.sup.4 is H, halogen, C.sub.1-C.sub.6 alkyl, phenyl, hydroxy or
C.sub.1-C.sub.6 alkoxy, then one R.sup.5 is other than halogen,
C.sub.1-C.sub.6 alkyl, hydroxy or C.sub.1-C.sub.6 alkoxy.
[0116] Also of note are methods for controlling arthropods
comprising contacting the arthropods or their environment with an
arthropodicidally effective amount of a compound of Formula IV and
insecticidal compositions thereof.
[0117] Preferred methods for reasons of better activity are:
[0118] Preferred 1. Methods comprising compounds of Formula 1
wherein J is a phenyl group substituted with 1 to 2 R.sup.5 and
optionally substituted with 1 to 3 R.sup.6.
[0119] Preferred 2. Methods of Preferred 1 wherein
[0120] A and B are both O;
[0121] n is 1 to 2;
[0122] R.sup.1 is H, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.2-C.sub.6 alkylcarbonyl or C.sub.2-C.sub.6
alkoxycarbonyl;
[0123] R.sup.2 is H, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.2-C.sub.6 alkylcarbonyl or C.sub.2-C.sub.6
alkoxycarbonyl;
[0124] R.sup.3 is C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl,
C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.6 cycloalkyl each
optionally substituted with one or more substituents selected from
the group consisting of halogen, CN, C.sub.1-C.sub.2 alkoxy,
C.sub.1-C.sub.2 alkylthio, C.sub.1-C.sub.2 alkylsulfinyl and
C.sub.1-C.sub.2 alkylsulfonyl;
[0125] one of the R.sup.4 groups is attached to the phenyl ring at
the 2-position or 5-position, and said R.sup.4 is C.sub.1-C.sub.4
alkyl C.sub.1-C.sub.4 haloalkyl, halogen, CN, NO.sub.2,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4
haloalkylsulfinyl or C.sub.1-C.sub.4 haloalkylsulfonyl;
[0126] each R.sup.5 is independently C.sub.1-C.sub.4 haloalkyl, CN,
NO.sub.2, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4 alkylthio,
C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl,
C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4 haloalkylsulfinyl,
C.sub.1-C.sub.4 haloalkylsulfonyl or C.sub.2-C.sub.4
alkoxycarbonyl; or
[0127] (R.sup.5).sub.2 when attached to adjacent carbon atoms can
be taken together as --OCF.sub.2O--, --CF.sub.2CF.sub.2O-- or
--OCF.sub.2CF.sub.2O--; and
[0128] each R.sup.6 is independently H, halogen, C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.2 alkoxy or C.sub.2-C.sub.4 alkoxycarbonyl,
or
[0129] each R.sup.6 is independently a phenyl or a 5- or 6-membered
heteroaromatic ring, each ring optionally substituted with
C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 haloalkynyl,
C.sub.3-C.sub.6 halocycloalkyl, halogen, CN, NO.sub.2,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.3-C.sub.6
(alkyl)cycloalkylamino, C.sub.2-C.sub.4 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl or C.sub.3-C.sub.6
trialkylsilyl.
[0130] Preferred 3. Methods of Preferred 2 wherein
[0131] R.sup.1 and R.sup.2 are both H;
[0132] R.sup.3 is C.sub.1-C.sub.4 alkyl optionally substituted with
halogen, CN, OCH.sub.3, S(O).sub.pCH.sub.3;
[0133] each R.sup.4 is independently H, CH.sub.3, CF.sub.3,
OCF.sub.3, OCHF.sub.2, S(O).sub.pCF.sub.3, S(O).sub.pCHF.sub.2, CN
or halogen;
[0134] each R.sup.5 is independently CF.sub.3, OCF.sub.3,
OCHF.sub.2, S(O).sub.pCF.sub.3, S(O).sub.pCHF.sub.2,
OCH.sub.2CF.sub.3, OCF.sub.2CHF.sub.2, S(O).sub.pCH.sub.2CF.sub.3
or S(O).sub.pCF.sub.2CHF.s- ub.2;
[0135] each R.sup.6 is independently H, halogen or methyl; or
phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each
ring optionally substituted with C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, halogen or CN; and p1 is 0, 1 or 2.
[0136] Preferred 4. Methods of Preferred 3 wherein R.sup.3 is
i-propyl or t-butyl.
[0137] Preferred 5. Methods comprising compounds of Formula 1
wherein J is a 5- or 6-membered heteroaromatic ring optionally
substituted with 1 to 4 R.sup.7.
[0138] Preferred 6. Methods of Preferred 5 wherein
[0139] J is a 5- or 6-membered heteroaromatic ring selected from
the group consisting of J-1, J-2, J-3, J-4 and J-5, each J
optionally substituted with 1 to 3 R.sup.7 7
[0140] Q is O, S or NR.sup.7; and
[0141] W, X, Y and Z are independently N or CR.sup.7, provided that
in J-4 and J-5 at least one of W, X, Y or Z is N.
[0142] Preferred 7. Methods of Preferred 5 or Preferred 6
wherein
[0143] A and B are O;
[0144] n is 1 to 2;
[0145] R.sup.1 is H, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.2-C.sub.6 alkylcarbonyl or
C.sub.2-C.sub.6 alkoxycarbonyl;
[0146] R.sup.2 is H, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.2-C.sub.6 alkylcarbonyl or C.sub.2-C.sub.6
alkoxycarbonyl;
[0147] R.sup.3 is H; or C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.6 cycloalkyl each
optionally substituted with one or more substituents selected from
the group consisting of halogen, CN, C.sub.1-C.sub.2 alkoxy,
C.sub.1-C.sub.2 alkylthio, C.sub.1-C.sub.2 alkylsulfinyl and
C.sub.1-C.sub.2 alkylsulfonyl;
[0148] one of the R.sup.4 groups is attached to the phenyl ring at
the 2-position, and said R.sup.4 is C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, halogen, CN, NO.sub.2, C.sub.1-C.sub.4
alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4 alkylthio,
C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl,
C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4 haloalkylsulfinyl,
or C.sub.1-C.sub.4 haloalkylsulfonyl; and
[0149] each R.sup.7 is independently H, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, halogen, CN, NO.sub.2, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
haloalkylthio, C.sub.1-C.sub.4 haloalkylsulfinyl, C.sub.1-C.sub.4
haloalkylsulfonyl or C.sub.2-C.sub.4 alkoxycarbonyl; or a phenyl or
a 5- or 6-membered heteroaromatic ring, each ring optionally
substituted with C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl.
[0150] Preferred 8. Methods of Preferred 7 wherein
[0151] J is selected from the group consisting of pyridine,
pyrimidine, pyrazole, imidazole, triazole, thiophene, thiazole and
oxazole, furan, isothiazole and isoxazole, each optionally
substituted with 1 to 3 R.sup.7.
[0152] Preferred 9. Methods of Preferred 8 wherein
[0153] J is selected from the group consisting of pyridine,
pyrimidine, pyrazole, thiophene and thiazole, each optionally
substituted with 1 to 3 R.sup.7;
[0154] R.sup.1 and R.sup.2 are both H;
[0155] R.sup.3 is C.sub.1-C.sub.4 alkyl optionally substituted with
halogen, CN, OCH.sub.3, S(O).sub.pCH.sub.3;
[0156] each R.sup.4 is independently H, CH.sub.3, CF.sub.3,
OCF.sub.3, OCHF.sub.2, S(O).sub.pCF.sub.3, S(O).sub.pCHF.sub.2, CN
or halogen;
[0157] each R.sup.7 is independently H, halogen, CH.sub.3,
CF.sub.3, OCHF.sub.2, S(O).sub.pCF.sub.3, S(O).sub.pCHF.sub.2,
OCH.sub.2CF.sub.3, OCF.sub.2CHF.sub.2, S(O).sub.pCH.sub.2CF.sub.3,
S(O).sub.pCF.sub.2CHF.sub- .2; or phenyl, pyrazole, imidazole,
triazole, pyridine or pyrimidine, each ring optionally substituted
with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, halogen or CN; and
[0158] p is 0, 1 or 2.
[0159] Preferred 10. Methods of Preferred 9 wherein J is a pyridine
optionally substituted with 1 to 3 R.sup.7.
[0160] Preferred 11. Methods of Preferred 10 wherein one R.sup.7 is
a phenyl optionally substituted with C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, halogen or CN.
[0161] Preferred 12. Methods of Preferred 10 wherein one R.sup.7 is
a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, halogen or CN.
[0162] Preferred 13. Methods of Preferred 9 wherein J is a
pyrimidine optionally substituted with 1 to 3 R.sup.7.
[0163] Preferred 14. Methods of Preferred 13 wherein one R.sup.7 is
a phenyl optionally substituted with C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, halogen or CN.
[0164] Preferred 15. Methods of Preferred 13 wherein one R.sup.7 is
a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, halogen or CN.
[0165] Preferred 16. Methods of Preferred 9 wherein J is a pyrazole
optionally substituted with 1 to 3 R.sup.7.
[0166] Preferred 17. Methods of Preferred 16 wherein one R.sup.7 is
a phenyl optionally substituted with C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, halogen or CN.
[0167] Preferred 18. Methods of Preferred 16 wherein one R.sup.7 is
a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, halogen or CN.
[0168] Preferred 19. Methods of Preferred 18 wherein R.sup.7 is a
pyridine optionally substituted with C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, halogen or CN.
[0169] Most preferred is the method comprising a compound of
Formula 1 selected from the group consisting of:
[0170]
3-methyl-N-(1-methylethyl)-2-[[4-(trifluoromethyl)benzoyl]amino]-be-
nzamide,
[0171]
2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]4-(tr-
ifluoromethyl)benzamide,
[0172]
2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-6-(t-
rifluoromethyl)-3-pyridinecarboxamide,
[0173]
1-ethyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(tr-
ifluoromethyl)-1H-pyrazole-5-carboxamide,
[0174]
1-(2-fluorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino)carbonyl]ph-
enyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,
[0175]
1-(3-chloro-2-pyridinyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbo-
nyl]phenyl]3-20 (trifluoromethyl)-1H-pyrazole-5-carboxamide,
[0176]
N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-
-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,
[0177]
3-bromo-1-(2-chlorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino]car-
bonyl]phenyl]-1H-pyrazole-5-carboxamide, and
[0178]
3-bromo-N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(2--
chlorophenyl)-1H-pyrazole-5-carboxamide.
[0179] Preferred compounds for reasons of better activity and/or
ease of synthesis are:
[0180] Preferred A. Compounds of Formula 1 wherein J is a phenyl
group substituted with 1 to 2 R.sup.5 and optionally substituted
with 1 to 3 R.sup.6.
[0181] Preferred B. Compounds of Preferred A wherein
[0182] A and B are both O;
[0183] n is 1 to 2;
[0184] R.sup.1 is H, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.2-C.sub.6 alkylcarbonyl or C.sub.2-C.sub.6
alkoxycarbonyl;
[0185] R.sup.2 is H, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.2-C.sub.6 alkylcarbonyl or C.sub.2-C.sub.6
alkoxycarbonyl;
[0186] R.sup.3 is C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl,
C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.6 cycloalkyl each
optionally substituted with one or more substituents selected from
the group consisting of halogen, CN, C.sub.1-C.sub.2 alkoxy,
C.sub.1-C.sub.2 alkylthio, C.sub.1-C.sub.2 alkylsulfinyl and
C.sub.1-C.sub.2 alkylsulfonyl;
[0187] one of the R.sup.4 groups is attached to the phenyl ring at
the 2-position or 5-position, and said R.sup.4 is C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.4 haloalkyl, halogen, CN, NO.sub.2,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4
haloalkylsulfinyl or C.sub.1-C.sub.4 haloalkylsulfonyl;
[0188] each R.sup.5 is independently C.sub.1-C.sub.4 haloalkyl, CN,
NO.sub.2, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4 alkylthio,
C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl,
C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4 haloalkylsulfinyl,
C.sub.1-C.sub.4 haloalkylsulfonyl or C.sub.2-C.sub.4
alkoxycarbonyl; or
[0189] (R.sup.5).sub.2 when attached to adjacent carbon atoms can
be taken together as --OCF.sub.2O--, --CF.sub.2CF.sub.2O-- or
--OCF.sub.2CF.sub.2O--; and
[0190] each R.sup.6 is independently H, halogen, C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.2 alkoxy or C.sub.2-C.sub.4 alkoxycarbonyl,
or
[0191] each R.sup.6 is independently a phenyl or a 5- or 6-membered
heteroaromatic ring, each ring optionally substituted with
C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 haloalkynyl,
C.sub.3-C.sub.6 halocycloalkyl, halogen, CN, NO.sub.2,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.3-C.sub.6
(alkyl)cycloalkylamino, C.sub.2-C.sub.4 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl or C.sub.3-C.sub.6
trialkylsilyl.
[0192] Preferred C. Compounds of Preferred B wherein
[0193] R.sup.1 and R.sup.2 are both H;
[0194] R.sup.3 is C.sub.1-C.sub.4 alkyl optionally substituted with
halogen, CN, OCH.sub.3, S(O).sub.pCH.sub.3;
[0195] each R.sup.4 is independently H, CH.sub.3, CF.sub.3,
OCF.sub.3, OCHF.sub.2, S(O).sub.pCF.sub.3, S(O).sub.pCHF.sub.2, CN
or halogen;
[0196] each R.sup.5 is independently CF.sub.3, OCF.sub.3,
OCHF.sub.2, S(O).sub.pCF.sub.3, S(O).sub.pCHF.sub.2,
OCH.sub.2CF.sub.3, OCF.sub.2CHF.sub.2, S(O).sub.pCH.sub.2CF.sub.3
or S(O).sub.pCF.sub.2CHF.s- ub.2;
[0197] each R.sup.6 is independently H, halogen or methyl; or
phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each
ring optionally substituted with C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, halogen or CN; and
[0198] p is 0, 1 or 2.
[0199] Preferred D. Compounds of Preferred C wherein R.sup.3 is
i-propyl or t-butyl.
[0200] Preferred E. Compounds of Formula 1 wherein J is a 5- or
6-membered heteroaromatic ring is optionally substituted with 1 to
4 R.sup.7.
[0201] Preferred F. Compounds of Preferred E wherein
[0202] J is a 5- or 6-membered heteroaromatic ring selected from
the group consisting of J-1, J-2, J-3, J-4 and J-5, each J
optionally substituted with 1 to 3 R.sup.7 8
[0203] Q is O, S or NR.sup.7; and
[0204] W, X, Y and Z are independently N or CR.sup.7, provided that
in J-4 and J-5 at least one of W, X, Y or Z is N.
[0205] Preferred G. Compounds of Preferred E or Preferred F
wherein
[0206] A and B are O;
[0207] n is 1 to 2;
[0208] R.sup.1 is H, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.2-C.sub.6 alkylcarbonyl or
C.sub.2-C.sub.6 alkoxycarbonyl;
[0209] R.sup.2 is H, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.2-C.sub.6 alkylcarbonyl or C.sub.2-C.sub.6
alkoxycarbonyl;
[0210] R.sup.3 is H; or C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.6 cycloalkyl each
optionally substituted with one or more substituents selected from
the group consisting of halogen, CN, C.sub.1-C.sub.2 alkoxy,
C.sub.1-C.sub.2 alkylthio, C.sub.1-C.sub.2 alkylsulfinyl and
C.sub.1-C.sub.2 alkylsulfonyl;
[0211] one of the R.sup.4 groups is attached to the phenyl ring at
the 2-position, and said R.sup.4 is C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, halogen, CN, NO.sub.2, C.sub.1-C.sub.4
alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4 alkylthio,
C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl,
C.sub.1-C.sub.4 haloalkylthio, C.sub.1-C.sub.4 haloalkylsulfinyl or
C.sub.1-C.sub.4 haloalkylsulfonyl; and
[0212] each R.sup.7 is independently H, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, halogen, CN, NO.sub.2, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
haloalkylthio, C.sub.1-C.sub.4 haloalkylsulfinyl, C.sub.1-C.sub.4
haloalkylsulfonyl or C.sub.2-C.sub.4 alkoxycarbonyl; or a phenyl or
a 5- or 6-membered heteroaromatic ring, each ring optionally
substituted with C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl.
[0213] Preferred H. Compounds of Preferred G wherein
[0214] J is selected from the group consisting of pyridine,
pyrimidine, pyrazole, imidazole, triazole, thiophene, thiazole and
oxazole, furan, isothiazole and isoxazole, each optionally
substituted with 1 to 3 R.sup.7.
[0215] Preferred I. Compounds of Preferred H wherein
[0216] J is selected from the group consisting of pyridine,
pyrimidine, pyrazole, thiophene and thiazole, each optionally
substituted with 1 to 3 R.sup.7;
[0217] R.sup.1 and R.sup.2 are both H;
[0218] R.sup.3 is C.sub.1-C.sub.4 alkyl optionally substituted with
halogen, CN, OCH.sub.3, S(O).sub.pCH.sub.3;
[0219] each R.sup.4 is independently H, CH.sub.3, CF.sub.3,
OCF.sub.3, OCHF.sub.2, S(O).sub.pCF.sub.3, S(O).sub.pCHF.sub.2, CN
or halogen;
[0220] each R.sup.7 is independently H, halogen, CH.sub.3,
CF.sub.3, OCHF.sub.2, S(O).sub.pCF.sub.3, S(O).sub.pCHF.sub.2,
OCH.sub.2CF.sub.3, OCF.sub.2CHF.sub.2, S(O).sub.pCH.sub.2CF.sub.3,
S(O).sub.pCF.sub.2CHF.sub- .2; or phenyl, pyrazole, imidazole,
triazole, pyridine or pyrimidine, each ring optionally substituted
with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, halogen or CN; and
[0221] p is 0, 1 or 2.
[0222] Preferred J. Compounds of Preferred I wherein J is a
pyridine optionally substituted with 1 to 3 R.sup.7.
[0223] Preferred K. Compounds of Preferred J wherein one R.sup.7 is
a phenyl optionally substituted with C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, halogen or CN.
[0224] Preferred L. Compounds of Preferred J wherein one R.sup.7 is
a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, halogen or CN.
[0225] Preferred M. Compounds of Preferred I wherein J is a
pyrimidine optionally substituted with 1 to 3 R.sup.7.
[0226] Preferred N. Compounds of Preferred M wherein one R.sup.7 is
a phenyl optionally substituted with C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, halogen or CN.
[0227] Preferred O. Compounds of Preferred M wherein one R.sup.7 is
a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, halogen or CN.
[0228] Preferred P. Compounds of Preferred I wherein J is a
pyrazole optionally substituted with 1 to 3 R.sup.7.
[0229] Preferred Q. Compounds of Preferred P wherein one R.sup.7 is
a phenyl optionally substituted with C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, halogen or CN.
[0230] Preferred R. Compounds of Preferred P wherein one R.sup.7 is
a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring
optionally substituted with C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, halogen or CN.
[0231] Preferred S. Compounds of Preferred R wherein R.sup.7 is a
pyridine optionally substituted with C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, halogen or CN.
[0232] Most preferred is the compound of Formula 1 selected from
the group consisting of:
[0233]
3-methyl-N-(1-methylethyl)-2-[[4-(trifluoromethyl)benzoyl]amino]-be-
nzamide,
[0234]
2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-4
(trifluoromethyl)benzamide,
[0235]
2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-6-(t-
rifluoromethyl)-3-pyridinecarboxamide,
[0236]
1-ethyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(tr-
ifluoromethyl)-1H-pyrazole-5-carboxamide,
[0237]
1-(2-fluorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino)carbonyl]ph-
enyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxaride,
[0238]
1-(3-chloro-2-pyridinyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbo-
nyl]phenyl]3-(trifluoromethyl)-1H-pyrarzole-5-carboxamide,
[0239]
N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-
-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,
[0240]
3-bromo-1-(2-chlorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino]car-
bonyl]phenyl]-1H-pyrazole-5-carboxamide, and
[0241]
3-bromo-N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(2--
chlorophenyl)-1H-pyrazole-5-carboxamide.
[0242] Preferred compositions are those comprising compounds of
formula 1 as preferred in Preferred 1 through 19, and the
specifically preferred compounds above.
[0243] As noted above, each J is independently a phenyl group or a
naphthyl group substituted with 1 to 2 R.sup.5 and optionally
substituted with 1 to 3 R.sup.6; or each J is independently a 5- or
6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered
fused heterobicyclic ring system wherein each ring or ring system
is optionally substituted with 1 to 4 R.sup.7. The term "optionally
substituted" in connection with these J groups refers to groups
which are unsubstituted or have at least one non-hydrogen
substituent that does not extinguish the arthropodicidal activity
possessed by the unsubstituted analog. Note also that J-1 through
J-5 above denote 5- or 6-membered heteroaromatic rings. An example
of phenyl substituted with 1 to 2 R.sup.5 and optionally
substituted with 1 to 3 R.sup.6 is the ring illustrated as J-6 in
Exhibit 1, wherein m is an integer from 1-2 and q is an integer
from 1 to 3. Note that at least one R.sup.5 must be present in J-6.
Although R.sup.6 groups are shown in the structure J-6, it is noted
that they do not need to be present since they are optional
substituents. An example of a naphthyl group substituted with 1 to
2 R.sup.5 and optionally substituted with 1 to 3 R.sup.6 is J-59
illustrated in Exhibit 1, wherein m is an integer from 1-2 and q is
an integer from 1 to 3. Note that at least one R.sup.5 must be
present in J-59. Although R.sup.6 groups are shown in the structure
J-59, it is noted that they do not need to be present since they
are optional substituents. Examples of 5- or 6-membered
heteroaromatic ring optionally substituted with 1 to 4 R.sup.7
include the rings J-7 through J-58 illustrated in Exhibit 1 wherein
r is an integer from 1 to 4. Note that J-7 through J-26 are
examples of J-1, J-27 through J41 are examples of J-2, J-42 through
J-44 are examples of J-3, J-46 through J-53 are examples of J-4 and
J-54 through J-58 are examples of J-5. The nitrogen atoms that
require substitution to fill their valence are substituted with
R.sup.7. Note that some J groups can only be substituted with less
than 4 R.sup.7 groups (e.g. J-19, J-20, J-23 through J-26 and J-37
through J-40 can only be substituted with one R.sup.7). Examples of
aromatic 8-, 9- or 10-membered fused heterobicyclic ring systems
optionally substituted with 1 to 4 R.sup.7 include J-60 through
J-90 illustrated in Exhibit 1 wherein r is an integer from 1 to 4.
Although R.sup.7 groups are shown in the structures J-7 through
J-58 and J-60 through J-90, it is noted that they do not need to be
present since they are optional substituents. Note that when
R.sup.5, R6 and/or R.sup.7 are H when attached to an atom, this is
the same as if said atom is unsubstituted. Note that when the
attachment point between (R.sup.5).sub.m, (R.sup.6).sub.q or
(R.sup.7).sub.r and the J group is illustrated as floating,
(R.sup.5).sub.m, (R.sup.6).sub.q or (R.sup.7).sub.r can be attached
to any available carbon atom of the J group. Note that when the
attachment point on the J group is illustrated as floating, the J
group can be attached to the remainder of Formula 1 through any
available carbon of the J group by replacement of a hydrogen atom.
9101112131415161718
[0244] As noted above, G is a 5- or 6-membered nonaromatic
carbocyclic or heterocyclic ring, optionally including one or two
ring members selected from the group consisting of C(.dbd.O), SO or
S(O).sub.2 and optionally substituted with 1 to 4 substituents
selected from the group consisting of C.sub.1-C.sub.2 alkyl,
halogen, CN, NO.sub.2 and C.sub.1-C.sub.2 alkoxy. The term
"optionally substituted" in connection with these G groups refers
to groups which are unsubstituted or have at least one non-hydrogen
substituent that does not extinguish the arthropodicidal activity
possessed by the unsubstituted analog. Note that when the
attachment point on the G group is illustrated as floating, the G
group can be attached to the remainder of Formula 1 through any
available carbon of the G group by replacement of a hydrogen atom.
The optional substituents can be attached to any available carbon
by replacing a hydrogen atom. Examples of 5- or 6-membered
nonaromatic carbocyclic rings as G include the rings illustrated as
G-1 through G-8 of Exhibit 2, wherein such rings are optionally
substituted with 1 to 4 substituents selected from the group
consisting of C.sub.1-C.sub.2 alkyl, halogen, CN, NO.sub.2 and
C.sub.1-C.sub.2 alkoxy. Examples of 5- or 6-membered nonaromatic
heterocyclic rings as G include the rings illustrated as G-9
through G-48 of Exhibit 2, wherein such rings are optionally
substituted with 1 to 4 substituents selected from the group
consisting of C.sub.1-C.sub.2 alkyl, halogen, CN, NO.sub.2 and
C.sub.1-C.sub.2 alkoxy. Note that when G comprises a ring selected
from G-31 through G-34, G-37 and G-38, Q.sup.1 is selected from O,
S or N. Note that when G is G-11, G13, G-14, G16, G-23, G-24, G-30
through G-34, G-37 and G-38 and Q.sup.1 is N, the nitrogen atom can
complete its valence by substitution with either H or
C.sub.1-C.sub.2 alkyl. 19202122
[0245] As noted above, each R.sup.6 and each R.sup.7 can be
independently (among others) 5- or 6-membered heteroaromatic rings
or aromatic 8-, 9- or 10-membered fused heterobicyclic ring
systems, each ring optionally substituted with one to three
substituents independently selected from the group consisting of
C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 haloalkynyl,
C.sub.3-C.sub.6 halocycloalkyl, halogen, CN, NO.sub.2,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4
alkylsulfonyl, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.8
dialkylamino, C.sub.3-C.sub.6 cycloalkylamino, C.sub.3-C.sub.6
(alkyl)cycloalkylamino, C.sub.2-C.sub.4 alkylcarbonyl,
C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminocarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl or C.sub.3-C.sub.6
trialkylsilyl. Examples of such R.sup.6 and R.sup.7 groups include
the rings or ring systems illustrated as rings J-7 through J-58 and
J-60 through J-90 illustrated in Exhibit 1, except that such rings
are optionally substituted with 1 to 3 substituents selected from
the group consisting of C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.3-C.sub.6 cycloalkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
halogen, CN, NO.sub.2, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio C.sub.1-C.sub.4
alkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.8 dialkylamino, C.sub.3-C.sub.6
cycloalkylamino, C.sub.3-C.sub.6 (alkyl)cycloalkylamino,
C.sub.2-C.sub.4 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.2-C.sub.6 alkylaminocarbonyl, C.sub.3-C.sub.8
dialkylaminocarbonyl or C.sub.3-C.sub.6 trialkylsilyl rather than
(R.sup.7).sub.r. Note that these substituents can be attached to
any available carbon atom of the J group by replacement of a
hydrogen atom. Note that when the attachment point on the J group
is illustrated as floating, the J group can be attached to the
remainder of Formula 1 through any available carbon of the J group
by replacement of a hydrogen atom.
[0246] One or more of the following methods and variations as
described in Schemes 1-17 can be used to prepare the compounds of
Formula 1. The definitions of A, B, J, R.sup.1, R.sup.2, R.sup.3,
R.sup.4, R.sup.5, R.sup.6, R.sup.7, m and n in the compounds of
Formulae 1-34 below are as defined above in the Summary of the
Invention. Compounds of Formulae 1a-c, 2a-b, 4a-g, 5a-b are various
subsets of the compounds of Formula 1, 2, 4 and 5.
[0247] Compounds of Formula 1 can be prepared by procedures
outlined in Schemes 1-17. A typical procedure is detailed in Scheme
1 and involves coupling of an anthranilic amide of Formula 2 with
an acid chloride of Formula 3 in the presence of an acid scavenger
to provide the compound of Formula 1a. Typical acid scavengers
include amine bases such as triethylamine, diisopropylethylamine
and pyridine; other scavengers include hydroxides such as sodium
and potassium hydroxide and carbonates such as sodium carbonate and
potassium carbonate. In certain instances it is useful to use
polymer-supported acid scavengers such as polymer-bound
diisopropylethylamine and polymer-bound dimetliylaminopyridine. In
a subsequent step, amides of Formula 1a can be converted to
thioamides of Formula 1b using a variety of standard thio transfer
reagents including phosphorus pentasulfide and Lawesson's reagent.
23
[0248] An alternate procedure for the preparation of compounds of
Formula 1a involves coupling of an anthranilic amide of Formula 2
with an acid of Formula 4 in the presence of a dehydrating agent
such as dicyclohexylcarbodiimide (DCC). Polymer supported reagents
are again useful here, such as polymer-bound
cyclohexylcarbodiimide. Synthetic procedures of Schemes 1 and 2 are
only representative examples of useful methods for the preparation
of Formula 1 compounds as the synthetic literature is extensive for
this type of reaction. 24
[0249] One skilled in the art will also realize that acid chlorides
of Formula 3 may be prepared from acids of Formula 4 by numerous
well-known methods.
[0250] Anthranilic amides of Formula 2a are typically available
from the corresponding 2-nitrobenzamides of Formula 5 via catalytic
hydrogenation of the nitro group. Typical procedures involve
reduction with hydrogen in the presence of a metal catalyst such as
palladium on carbon or platinum oxide and in hydroxylic solvents
such as ethanol and isopropanol. These procedures are well
documented in the chemical literature. R.sup.1 substituents such as
alkyl, substituted alkyl and the like can generally be introduced
at this stage through known procedures including either direct
alkylation or through the generally preferred method of reductive
alkylation of the amine. A commonly employed procedure is to
combine the aniline 2a with an aldehyde in the presence of a
reducing agent such as sodium cyanoborohydride to produce the
Formula 2b compounds where R.sup.1 is alkyl, alkenyl, alkynyl or
substituted derivatives thereof. 25
[0251] The intermediate amides of Formula 5a are readily prepared
from commercially available 2-nitrobenzoic acids. Typical methods
for amide formation can be applied here. These include direct
dehydrative coupling of acids of Formula 6 with amines of Formula 7
using for example DCC, and conversion of the acids to an activated
form such as the acid chlorides or anhydrides and subsequent
coupling with amines to form amides of Formula 5a. We have found
ethylchloroformate to be an especially useful reagent for this type
of reaction involving activation of the acid. The chemical
literature is extensive on this type of reaction. Amides of Formula
5a are readily converted to thioamides of Formula 5b by using
commercially available thio transfer reagents such as phosphorus
pentasulfide and Lawesson's reagent. 26
[0252] Benzoic acids of Formula 4 (J is optionally substituted
phenyl) are generally well known in the art as are procedures for
their preparation. One particularly useful subset of benzoic acids
of this invention are 2-methyl-4-perfluoroalkyl benzoic acids of
Formula 4a (R.sup.5 equals e.g. CF.sub.3, C.sub.2F.sub.5,
C.sub.3F.sub.7). The synthesis for these compounds is outlined in
Schemes 5-9. Benzoic acids of Formula 4a may be prepared from the
benzonitriles of Formula 8 by hydrolysis. The conditions used may
involve the use of a base such as an alkaline metal hydroxide or
alkoxide (e.g. potassium or sodium hydroxide) in a solvent such as
water, ethanol or ethylene glycol (e.g. J. Chem. Soc. 1948, 1025).
Alternatively, the hydrolysis may be carried out using an acid such
as sulfuric acid or phosphoric acid in a suitable solvent such as
water (e.g. Org. Synth. 1955, Coll vol. 3, 557). The choice of the
conditions is contingent on the stability of R.sup.5 to the
reaction conditions and elevated temperatures are usually employed
to achieve this transformation. 27
[0253] Nitriles of Formula 8 may be prepared from anilines of
Formula 9 by the classical sequence involving diazotization and
treatment of the intermediate diazonium salt with a copper cyanide
salt (e.g. J. Amer. Chem. Soc. 1902, 24, 1035). 28
[0254] Anilines of Formula 9 may be prepared from compounds of
Formula 10. This transformation may be achieved by a well-known
procedure that employs Raney Nickel (Org. Synth. Coll. Vol VI,
581). Alternatively, the same transformation may be effected by the
use of a suitable catalyst such as palladium in the presence of
hydrogen. The reaction is usually conducted at pressures of
10.sup.2 to 10.sup.5 kPa in a suitable organic solvent such as, but
not limited to, toluene. Elevated temperatures of 80-110.degree. C.
are usually required to achieve the transformation. As one skilled
in the art will realize, numerous chemical modifications of the
thioether moiety are possible, and may be employed when necessary
to facilitate this transformation. 29
[0255] Compounds of Formula 10 may be prepared from iminosulfuranes
of Formula 11. The transformation may be achieved in a protic
solvent such as methanol or water, in a non-protic solvent such as
dichloromethane or toluene in the presence of a suitable base such
as triethylamine (e.g. Org. Synth. Coll. Vol. VI, 581) or sodium
methoxide, or in a combination of a protic solvent, a protic
solvent and a base. The temperature at which the reaction is
conducted is usually in the range 40-110.degree. C. As one skilled
in the art will realize, suitable salts of compounds of Formula 11
such as, but not limited to a hydrochloride, a sulfate or a
bisulfate may also be employed, provided that the appropriate
amount of base is first used to generate the free base 11. This may
be done as a separate step or as an integral part of the step
involving the transformation of compounds of Formula 11 to
compounds of Formula 10. 30
[0256] Compounds of Formula 11 may be prepared from anilines of
Formula 12 by reaction with dimethyl sulfide and a suitable
chlorinating agent such as, but not limited to N-chlorosuccinimide
(e.g. Org. Synth. Coll. Vol. VI, 581), chlorine or
N-chlorobenzotriazole. Alternatively, anilines of Formula 12 may be
treated with dimethyl sulfoxide which has been "activated" by
treatment with an agent such as acetic anhydride, trifluoroacetic,
anhydride, trifluoromethanesulfonic anhydride,
cyclohexylcarbodiimide, sulfur trioxide, or phosphorus pentoxide.
The reaction is conducted in a suitable organic solvent such as
dichloromethane or dimethyl sulfoxide. The reaction is conducted at
a temperature of -70.degree. C. to 25.degree. C. and is dependent
on the solvent and reagent used. 31
[0257] Intermediate anthranilic amides of Formula 2a and 2b may
also be prepared from isatoic anhydrides of Formula 13 and 14
(Scheme 10). Typical procedures involve combination of equimolar
amounts of the amine 7 with the isatoic anhydride in polar aprotic
solvents such as pyridine and dimethylformamide at temperatures
ranging from room temperature to 100.degree. C. R.sup.1
substituents such as alkyl and substituted alkyl may be introduced
by the base catalyzed alkylation of isatoic anhydride 13 with known
alkylating reagents R.sup.1-Lg (wherein Lg is a leaving group such
as halogen, alkyl or aryl suphonates or alkyl sulfates) to provide
the alkyl substituted intermediates 14. Isatoic anhydrides of
Formula 13 may be made by methods described in Coppola, Synthesis
505-36 (1980). 32
[0258] An alternate procedure for the preparation of specific
compounds of Formula 1 (where A is O, B is O and R.sup.1 is H)
involves reaction of an amine 7 with a benzoxazinone of Formula 15.
Typical procedures involve combination of the amine with the
benzoxazinone in solvents such as tetrahydrofuran or pyridine at
temperatures ranging from room temperature to the reflux
temperature of the solvent. Benzoxazinones are well documented in
the chemical literature and are available via known methods that
involve the coupling of either an anthranilic acid or an isatoic
anhydride with an acid chloride. For references to the synthesis
and chemistry of Benzoxazinones see Jakobsen et al, Biorganic and
Medicinal Chemistry, 2000, 8, 2095-2103 and references cited
within. See also Coppola, J. Heterocyclic Chemistry, 1999, 36,
563-588. 33
[0259] Heterocyclic acids 4, where J is equal to an optionally
substituted heterocycle, can be prepared by procedures outlined in
Schemes 12-17. Both general and specific references to a wide
variety of heterocyclic acids including thiophenes, furans,
pyridines, pyrimidines, triazoles, imidazoles, pyrazoles,
thiazoles, oxazoles, isothiazoles, thiadiazoles, oxadiazoles,
triazines, pyrazines, pyridazines, and isoxazoles can be found in
the following compendia: Rodd's Chemistry of Chemistry of Carbon
Compounds, Vol. IVa to IVl., S. Coffey editor, Elsevier Scientific
Publishing, New York, 1973; Comprehensive Heterocyclic Chemistry,
Vol. 1-7, A. R. Katritzky and C. W. Rees editors, Pergamon Press,
New York, 1984; Comprehensive Heterocyclic Chemistry II, Vol. 1-9,
A. R. Katritzky, C. W. Rees, and E. F. Scriven editors, Pergamon
Press, New York, 1996; and the series, The Chemistry of
Heterocyclic Compounds, E. C. Taylor, editor, Wiley, New York.
Particularly useful heterocyclic acids of this invention include
pyridine acids, pyrimidine acids and pyrazole acids. Procedures for
the synthesis of representative examples of each are detailed in
Schemes 12-17. A variety of heterocyclic acids and general methods
for their synthesis may be found in World Patent Application WO
98/57397.
[0260] The synthesis of representative pyridine acids (4b) is
depicted in Scheme 12. This procedure involves the known synthesis
of pyridines from ,.beta.-ketoesters and 4-aminobutenones (19).
Substituent groups R.sup.7(a) and R.sup.7(b) include e.g. alkyl and
haloalkyl. 34
[0261] The synthesis of representative pyrimidine acids (4c) is
depicted in Scheme 13. This procedure involves the known synthesis
of pyrimidines from vinylidene-.beta.-ketoesters (22) and amidines.
Substituent groups R.sup.7(a) and R.sup.7(b) include e.g. alkyl and
haloalkyl. 35
[0262] The synthesis of representative pyrazole acids (4d-4g) is
depicted in Schemes 14-17. Pyrazoles 4d are described in Scheme 14.
The synthesis of Scheme 14 involves as the key step introduction of
the R.sup.7(b) substituent via alkylation of the pyrazole. The
alkylating agent R.sup.7(b)-Lg (wherein Lg is a leaving group such
as Cl, Br, I, sulfonates such as p-toluenesulfonate or
methanesulfonate or sulfates such as --SO.sub.2OR.sup.7(b))
includes R.sup.7(b) groups such as C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6
cycloalkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 haloalkynyl, C.sub.3-C.sub.6 halocycloalkyl,
C.sub.2-C.sub.6 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl,
C.sub.3-C.sub.8 dialkylaminocarbonyl, C.sub.3-C.sub.6
trialkylsilyl; or phenyl, benzyl, benzoyl, 5- or 6-membered
heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused
heterobicyclic ring system, each ring or ring system optionally
substituted. Oxidation of the methyl group affords the pyrazole
carboxylic acid. Some of the more preferred R.sup.7(a) groups
include haloalkyl. 36
[0263] Pyrazoles 4e are described in Scheme 15. These pyrazole
acids may be prepared via metallation and carboxylation of
pyrazoles of formula 28 as the key step. The R.sup.7(b) group is
introduced in a manner similar to that of Scheme 14, i.e. via
alkylation with a R.sup.7(b) alkylating agent. Representative
R.sup.7(a) groups include e.g. cyano, and haloalkyl. 37
[0264] Pyrazoles 4f are described in Scheme 16. These can be
prepared via reaction of an optionally substituted phenyl hydrazine
29 with a pyruvate 30 to yield pyrazole esters 31. Hydrolysis of
the ester affords the pyrazole acids 4f. This procedure is
particularly useful for the preparation of compounds where
R.sup.7(b) is optionally substituted phenyl and R.sup.7(a) is
haloalkyl. 38
[0265] Pyrazoles acids of Formula 4g are described in Scheme 17.
These can be prepared via 3+2 cycloaddition of an appropriately
substituted nitrilimine with either substituted propiolates (33) or
acrylates (36). Cycloaddition with acrylates requires additional
oxidation of the intermediate pyrazoline to the pyrazole.
Hydrolysis of the ester affords the pyrazole acids 4g. Preferred
iminohalides for this reaction include the trifluoromethyl
iminochloride (38) and the iminodibromide (39). Compounds such as
38 are known (J. Heterocycl. Chem. 1985, 22(2), 565-8). Compounds
such as 39 are available by known methods (Tetrahedron Letters
1999, 40, 2605). These procedures are particularly useful for the
preparation of compounds where R.sup.7(b) is optionally substituted
phenyl and R.sup.7(a) is haloalkyl or bromo. 39
[0266] It is recognized that some reagents and reaction conditions
described above for preparing compounds of Formula I may not be
compatible with certain functionalities present in the
intermediates. In these instances, the incorporation of
protection/deprotection sequences or functional group
interconversions into the synthesis will aid in obtaining the
desired products. The use and choice of the protecting groups will
be apparent to one skilled in chemical synthesis (see, for example,
Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic
Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art
will recognize that, in some cases, after the introduction of a
given reagent as it is depicted in any individual scheme, it may be
necessary to perform additional routine synthetic steps not
described in detail to complete the synthesis of compounds of
Formula 1. One skilled in the art will also recognize that it may
be necessary to perform a combination of the steps illustrated in
the above schemes in an order other than that implied by the
particular sequence presented to prepare the compounds of Formula
1.
[0267] One skilled in the art will also recognize that compounds of
Formula 1 and the intermediates described herein can be subjected
to various electrophilic, nucleophilic, radical, organometallic,
oxidation, and reduction reactions to add substituents or modify
existing substituents.
[0268] Without further elaboration, it is believed that one skilled
in the art using the preceding description can utilize the present
invention to its fullest extent. The following Examples are,
therefore, to be construed as merely illustrative, and not limiting
of the disclosure in any way whatsoever. Percentages are by weight
except for chromatographic solvent mixtures or where otherwise
indicated. Parts and percentages for chromatographic solvent
mixtures are by volume unless otherwise indicated. .sup.1H NMR
spectra are reported in ppm downfield from tetramethylsilane; s is
singlet, d is doublet, t is triplet, q is quartet, m is multiplet,
dd is doublet of doublets, dt is doublet of triplets, br s is broad
singlet.
EXAMPLE 1
[0269] Step A: Preparation of
3-methyl-N-(1-methylethyl)-2-nitrobenzamide
[0270] A solution of 3-methyl-2-nitrobenzoic acid (2.00 g, 11.0
mmol) and triethylamine (1.22 g, 12.1 mmol) in 25 mL of methylene
chloride was cooled to 10.degree. C. Ethyl chloroformate was
carefully added and a solid precipitate formed. After stirring for
30 minutes isopropylamine (0.94 g, 16.0 mmol) was added and a
homogeneous solution resulted. The reaction was stirred for an
additional hour, poured into water and extracted with ethyl
acetate. The organic extracts were washed with water, dried over
magnesium sulfate and evaporated under reduced pressure to afford
1.96 g of the desired intermediate as a white solid melting at
126-128.degree. C.
[0271] .sup.1H NMR (CDCl.sub.3) .delta. 1.24 (d,6H), 2.38 (s,3H),
4.22 (m,1H), 5.80 (br s,1H), 7.4 (m,3H).
[0272] Step B: Preparation of
2-amino-3-methyl-N-(1-methylethyl)benzamide
[0273] The 2-nitrobenzamide of Step A (1.70 g, 7.6 mmol) was
hydrogenated over 5% Pd/C in 40 mL of ethanol at 50 psi. When the
uptake of hydrogen ceased the reaction was filtered through celite
and the celite was washed with ether. The filtrate was evaporated
under reduced pressure to afford 1.41 g of the title compound as a
solid melting at 149-151.degree. C.
[0274] .sup.1H NMR (CDCl.sub.3) .delta. 1.24 (dd,6H), 2.16 (s,3H),
4.25 (m,1H), 5.54 (br s,2H), 5.85 (br s,1H), 6.59 (t,1H), 7.13
(d,1H), 7.17 (d,1H).
[0275] Step C: Preparation of
3-methyl-N-(1-methylethyl)-2-[[4-(trifluorom-
ethoxy)benzoyl]amino]benzamide
[0276] 4-(trifluoromethoxy)benzoyl chloride (0.29 g, 1.3 mmol) was
added dropwise to a mixture of the aniline from Step B (0.25 g, 1.3
mmol) and triethylamine (0.13 g, 1.3 mmol) in 5 mL of methylene
chloride at room temperature. After stirring for one hour the
reaction was poured into water and extracted with ethyl acetate.
The combined extracts were dried over magnesium sulfate and
evaporated under reduced pressure. The resulting solids were washed
with hexane/ether and filtered to afford 0.41 g of the title
compound, a compound of the present invention, as a solid melting
at 207-209.degree. C.
[0277] .sup.1H NMR (CDCl.sub.3) 67 1.19 (d, 6H), 2.33 (s, 3H), 4.15
(m, 1H), 5.97 (br d, 1H), 7.2-7.4 (m, 6H), 8.04 (d, 1H), 10.11 (br
s, 1H).
EXAMPLE 2
[0278] Step A: Preparation of 1-Ethyl-3-trifluoromethylpyrazol-5-yl
Carboxylic Acid
[0279] To a mixture of 3-trifluoromethylpyrazole (5 g, 37 mmol) and
powdered potassium carbonate (10 g, 72 mmol) stirring in 30 mL of
N,N-dimethylformamide, iodoethane (8 g, 51 mmol) was added
dropwise. After a mild exotherm, the reaction was stirred overnight
at room temperature. The reaction mixture was partitioned between
100 mL of diethyl ether and 100 mL of water. The ether layer was
separated, washed with water (3.times.) and brine, and dried over
magnesium sulfate. Evaporation of solvent in vacuo gave 4 g of
oil.
[0280] To 3.8 g of this oil stirring in 40 mL of tetrahydrofuran
under nitrogen in a dry ice/acetone bath, 17 mL of a 2.5 M solution
of n-butyl lithium in tetrahydrofuran (43 mmol) was added dropwise
and the solution stirred for 20 minutes at -78.degree. C. An excess
of gaseous carbon dioxide was bubbled into the stirred solution at
a moderate rate for 10 minutes. After addition of carbon dioxide,
the reaction was allowed to slowly reach room temperature and
stirred overnight. The reaction mixture was partitioned between
diethyl ether (100 mL) and 0.5 N aqueous sodium hydroxide (100 mL).
The basic layer was separated and acidified with concentrated
hydrochloric acid to a pH of 2-3. The aqueous mixture was extracted
with ethyl acetate (100 mL) and the organic extract washed with
water and brine and dried over magnesium sulfate. The oily residue,
which remained after evaporating the solvent in vacuo, was
triturated to a solid from a small amount of n-butyl chloride.
After filtering and drying, a slightly impure, sample of
1-ethyl-3-trifluoromethyl-pyrazol-5-- yl carboxylic acid (1.4 g)
was obtained as a broad-melting solid.
[0281] 1H NMR (CDCl.sub.3): 9.85 (br s,1H), 7.23 (s,1H), 4.68
(q,2H), 1.51 (t,3H) ppm.
[0282] Step B: Preparation of
2-[1-Ethyl-3-trifluoromethylpyrazol-5-yl
carbamoyl]-3-methyl-N-(1-methylethyl)benzamide
[0283] To a solution of 1-ethyl-3-trifluoromethyl-pyrazol-5-yl
carboxylic acid (0.5 g, 2.4 mmol) stirring in 20 mL of methylene
chloride, oxalyl chloride (1.2 mL, 14 mmol) was added. Upon
addition of 2 drops of N,N-dimethylformamide, foaming and bubbling
occurred. The reaction mixture was heated at reflux for 1 hr as a
yellow solution. After cooling, the solvent was removed in vacuo
and the resulting residue dissolved in 20 mL of tetrahydrofuran. To
the stirred solution, 2-amino-3-methyl-N-(1-methylethyl)benzamide
(0.7 g, 3.6 mmol) was added followed by the dropwise addition of
N,N-diisopropylethylamine (3 mL, 17 mmol). After stirring at room
temperature overnight, the reaction mixture was partitioned between
ethyl acetate (100 mL) and 1N aqueous hydrochloric acid (75 mL).
The separated organic layer was washed with water and brine and
dried over magnesium sulfate. Evaporating in vacuo gave a white
solid residue, which on purification by flash column chromatography
on silica gel (2:1 hexanes/ethyl acetate) afforded 0.5 g of the
title compound, a compound of the present invention, melting at
223-226.degree. C.
[0284] .sup.1H NMR (DMSO-D.sub.6): 10.15 (s,1H), 8.05 (d,1H), 7.45
(s,1H), 7.43-7.25 (m,3H), 4.58 (q,2H), 3.97 (m,1H), 2.45 (s,3H),
1.36 (t,3H), 1.06 (d,6H) ppm.
EXAMPLE 3
[0285] Step A: Preparation of
S,S-dimethyl-N-[4-(trifluoromethyl)phenyl]su- lfilimine
[0286] A solution of N-chlorosuccinimide (12-43 g, 93.1 mmol) in
.about.170 mL of dichloromethane was added to a mixture of
4-(trifluoromethyl) aniline (15 g, 93.1 mmol) and dimethyl sulfide
(6.35 g, 102 mmol) in 230 mL of dichloromethane at -5-0.degree. C.
After the addition was complete, the mixture was stirred at
0-5.degree. C. for 1 h, and N-chlorosuccinimide (0.02 g, 4.64 mmol)
was added. After a further 30 minutes, the mixture was washed with
500 mL of 1N sodium hydroxide.
[0287] The organic phase was dried and evaporated to give the
product as a solid 19-72 g melting at 101-103.degree. C. (after
crystallization from ethyl acetate/hexanes).
[0288] IR(Nujol) 1603, 1562, 1532, 1502, 1428, 1402, 1335, 1300,
1270, 1185, 1150, 1103, 1067, 1000, 972, 940, 906, 837, 817
cm.sup.-1.
[0289] .sup.1H NMR (CDCl.sub.3) .delta. 7.35 (d, J=8.8 Hz, 2 H),
6.84 (d, J=8.8 Hz, 2 H), 2.67 (5, 3 H).
[0290] Step B:
2-[(methylthio)methyl]-4-(trifluoromethyl)benzenamine
[0291] Sodium methoxide in methanol (1.95 g, 9.02 mmol, 25%) was
added to S,S-dimethyl-N-[4-(trifluoromethyl)phenyl]sulfilimine from
Step A (2 g, 9.04 mmol) in 15 mL of toluene. The mixture was warmed
to .about.80.degree. C. for .about.1 h. The mixture was allowed to
cool to 25.degree. C. and was poured into 100 mL of water. The
mixture was extracted with 2.times.100 mL of ethyl acetate and the
combined extracts were dried and evaporated to give 1.8 g of the
product as a solid melting at 65.5-67.5.degree. C. (after
crystallization from hexanes).
[0292] IR(nujol) 3419, 3333, 1629, 1584, 1512, 1440, 1334, 1302,
1235, 1193, 1139, 1098, 1078, 979, 904, 832 cm.sup.-1.
[0293] .sup.1.sup.1H NMR (CDCl.sub.3) .delta. 7.35 (dd, J=1.5
Hz.times.8.2 Hz, 1H) 6.72 (d, J=8.4 Hz) 4.39 (br.5 2 H, 3.69 (5, 2
H), 1.99 (5, 3 H).
[0294] Step C: Preparation of
2-methyl-4-(trifluoromethyl)benzenamine
[0295] Activated Raney nickel (500 g wet paste, .about.50.mu.) was
added portionwise to a solution of
2-[(methylthio)methyl]-4-(trifluoromethyl)be- nzenamine (55.3 g,
0.25 mole) in 1 L of ethanol over 30 minutes at 25-30.degree. C.
The heterogeneous mixture was stirred vigorously for 30 minutes
after the addition. The stirring was stopped, and the solids were
allowed to settle over one hour. The liquid was decanted from the
solids and poured through filter paper. The filtrate was evaporated
under reduced pressure, and the residue was taken up in
dichloromethane. The organic phase was separated from a small
volume of water, dried over magnesium sulfate and evaporated under
reduced pressure to afford 37.6 g of the title compound as amber
oil.
[0296] .sup.1H NMR (CDCl.sub.3) 67 7.28 (m,2H), 6.68 (d,1H), 3.87
(br s,2H), 2.19 (s,3H).
[0297] Step D: Preparation of 2-methyl
(trifluoromethyl)benzonitrile
[0298] Concentrated hydrochloric acid (16 mL) was added dropwise at
a moderate rate to a heterogeneous mixture of
2-methyl-4-(trifluoromethyl)b- enzenamine (14 g, 80 mmol) and 120
mL of water while stirring vigorously. A thick suspension resulted
which was stirred for 20 minutes, diluted with 280 mL of water and
cooled to 5.degree. C. A solution of sodium nitrite (5.5 g, 80
mmol) and 25 mL of water was added slowly to the reaction
suspension. After stirring for 30 minutes at 5.degree. C. a
solution resulted which was stirred cold for 30 more minutes and
then neutralized with potassium carbonate. This diazonium salt
solution was then added portionwise via cannula to a stirred,
95.degree. C. mixture of potassium cyanide (22 g, 0.34 mole),
copper sulfate pentahydrate (20 g, 80 mmol) and 140 mL of water.
After the addition the mixture was stirred for 30 minutes at
95.degree. C. and then allowed to cool to room temperature. Ether
was added and the heterogeneous mixture was filtered through
celite. The solids were washed with ether, and the filtrate was
partitioned. The aqueous phase was extracted with ether, and the
combined organic extracts were dried over magnesium sulfate and
concentrated under reduced pressure to afford 13.1 g of the title
compound as brown oil.
[0299] .sup.1H NMR (CDCl.sub.3) .delta. 7.74 (d,1H), 7.60 (s,1H),
7.55 (d,1H), 2.64 (s,3H).
[0300] Step E: Preparation of 2-methyl-4-trifluoromethyl benzoic
Acid
[0301] Potassium hydroxide (15.7 g, 0.28 mole) and 15 mL of water
were added as a solution to a stirred, heterogeneous mixture of
2-methyl-4-(trifluoromethyl)benzonitrile (13 g, 70 mmol) and 135 mL
of ethylene glycol. The reaction mixture was heated at
120-130.degree. C. for 20 hours and allowed to cool to room
temperature. The dark solution was poured into 800 mL of water and
filtered through celite. The filtrate was washed with ether and
then the aqueous was acidified with concentrated hydrochloric acid.
This aqueous phase was extracted three times with ethyl acetate,
the organic extracts were combined, dried over magnesium sulfate
and evaporated under reduced pressure to afford the title compound
as a tan solid.
[0302] .sup.1H NMR (CDCl.sub.3) 67 7.98 (d,1H), 7.70 (s,1H), 7.65
(d,1H), 2.60 (s,3H).
[0303] Step F: Preparation of 2-methyl-4-(trifluoromethoxy)benzoyl
chloride
[0304] Thionyl chloride (0.42 g, 3.5 mmol) was added to a solution
of the benzoic acid from Step E (0.50 g, 2.4 mmol) in 10 mL of
toluene at room temperature. The reaction was refluxed for three
hours then cooled to room temperature. The solvent was evaporated
under reduced pressure and excess thionyl chloride was removed by
azeotroping with toluene. The benzoyl chloride obtained was used
directly in Step G.
[0305] Step G: Preparation of
2-methyl-N-[2-methyl-6-[[(1-methylethyl)amin-
o]-carbonyl]phenyl]-4-(trifluoromethyl)benzamide
[0306] The benzoyl chloride of Step F (0.29 g, 1.3 mmol) was added
to a mixture of the aniline from Example 1, Step B (0.36 g, 1.9
mmol) and diisopropylethylamine (0.26 g, 2.0 mmol) in 10 mL of
chloroform at room temperature. The reaction was allowed to stir
overnight. The solid precipitate was filtered and dried to afford
0.38 g of the title compound, a compound of the present invention,
as a solid melting at 247-248.degree. C.
[0307] .sup.1H NMR (CDCl.sub.3) .alpha. 1.24 (d,6H), 2.41 (s,3H),
2.58 (s,3H), 4.20 (m,1H), 5.94 (br d,1H), 7.2-7.3 (m,2H), 7.40
(d,1H), 7.52 (s,1H), 7.53 (d,1H), 7.70 (d,1H), 9.36 (br s,1H).
EXAMPLE 4
[0308] Step A: Preparation of
2-Methyl-6-(trifluoromethyl)-3-pyridinecarbo- nyl chloride
[0309] Thionyl chloride (4.35 g, 36.5 mmol) was added to a mixture
of 2-methyl-6-trifluoromethyl nicotinic acid (5.00 g, 24.4 mmol) in
75 mL of toluene and the mixture was heated at reflux for 3 hours.
The reaction was cooled to room temperature and the solvent was
removed under reduced pressure. Excess thionyl chloride was removed
by azeotrope with toluene. The resultant acid chloride was used as
is in Example 4, Step B.
[0310] Step B: Preparation of
8-Methyl-2-[2-methyl-6-(trifluoromethyl)-3-p-
yridinyl]-4H-3,1-benzoxazine
[0311] A mixture of the 6-methyl isatoic anhydride (3.92 g, 22.1
mmol) and the acid chloride from Step A (5.45 g, 24.3 mmol) was
heated at reflux in pyridine for 16 hours. The dark brown solution
was cooled to room temperature and the solvent was removed under
reduced pressure. Excess pyridine was removed by azeotrope with
toluene. Ether was added and the resulting brown solid was removed
by filtration. The solid was taken up in a mixture of aqueous
sodium bicarbonate and chloroform, the chloroform extracts were
dried over magnesium sulfate and evaporated. Excess pyridine was
again removed by azeotrope with toluene to afford 5.1 g of the
title compound as a brown solid.
[0312] .sup.1H NMR (CDCl.sub.3) d 2.65 (s,3H), 3.11 (s,3H), 7.49
(t,1H) 7.40 (m,1H), 7.68-7.73 (m,2H), 1.11 (d,1H), 8.58 (d,1H).
[0313] Step C: Preparation of
2-Methyl-N-[2-methyl-6-[[(1-methylethyl)amin-
o]carbonyl]phenyl]-6-(trifluoromethyl)-3-pyridine
[0314] Isopropylamine (7.37 g, 0.125 mmol) was added to a mixture
of the benzoxazinone of Step B (4.00 g, 12.5 mmol) in 30 mL of
tetrahydrofuran. A homogeneous solution formed. The mixture was
heated briefly after which a thick white precipitate formed. The
solvent was removed under reduced pressure and the resultant solid
was washed with ether and filtered to afford 4.48 g of the title
compound as a solid melting at 247-248.degree. C.
[0315] .sup.1H NMR (CDCl.sub.3) d 1.24 (d,6H), 2.41 (s,3H), 2.77
(s,3H), 4.17 (m,1H), 5.96 (b,d,1H), 7.21 (m,2H) 7.40 (m,1H), 7.53
(d,1H), 7.97 (d,1H), 9.80 (bs,1H).
EXAMPLE 5
[0316] Step A: Preparation of
4-Methyl-N-[2-methyl-6-[[(1-methylethyl)amin-
o]carbonyl]phenyl]-2-(trifluoromethyl)-5-primidinecarboxamide
[0317] To a solution 0.8 g (4 mmol) of
4-methyl-2-tritluoromethylpyrimidin- e-5-carboxylic acid [made by
the method of Palanki et al, J. Med. Chem. 2000, 43, 3995] stirring
in 15 mL of methylene chloride, oxalyl chloride (2 mL, 23 mmol) was
added. Upon addition of 2 drops of N,N-dimethylformamide, foaming
and bubbling occurred. The reaction mixture was heated at reflux
for 1 hr as a yellow solution. After cooling, the solvent was
removed in vacuo and the resulting residue dissolved in 20 mL of
tetrahydrofuran. To the stirred solution,
2-amino-3-methyl-N-(1-methylethyl)benzamide (1 g, 5 mmol) was added
followed by the dropwise addition of N,N-diisopropylethylamine (3
ml, 17 mmol). After stirring at room temperature overnight, the
reaction mixture was partitioned between ethyl acetate (200 mL) and
1N aqueous hydrochloric acid (75 mL). The separated organic layer
was washed with water and brine and dried over magnesium sulfate.
Evaporating in vacuo gave a white solid, which was suspended in a
small amount of ethyl acetate and filtered to afford (after drying)
650 mg of the title compound, a compound of the present invention,
melting at 248-251.degree. C.
[0318] .sup.1H NMR (DMSO-D.sub.6): 10.3 (s,NH), 9.07 (s,1H), 8.25
(d,NH), 7.43-7.25 (m,3H), 4.03 (m,1H), 2.73 (s,3H), 2.32 (s,3H),
1.12 (d,6H) ppm.
EXAMPLE 6
[0319] Step A: Preparation of
2-Methyl-1-phenyl-4-(trifuoromethyl)-1H-pyra- zole
[0320] A solution of 1,1,1-trifluoropentane-2,4-dione (20.0 g,
0.130 mole) in glacial acetic acid (60 mL) was cooled to 7.degree.
C. using an ice/water bath. Phenylhydrazine (14.1 g, 0.130 mole)
was added dropwise over a period of 60 minutes. The reaction mass
temperature increased to 15.degree. C. during the addition. The
resulting orange solution was held under ambient conditions for 60
minutes. The bulk of the acetic acid was removed by stripping on a
rotary evaporator at a bath temperature of 65.degree. C. The
residue was dissolved in methylene chloride (150 mL). The solution
was washed with aqueous sodium bicarbonate (3 g in 50 mL water).
The purple-red organic layer was separated, treated with activated
charcoal (2 g) and MgSO.sub.4, then filtered. Volatiles were
removed on a rotary evaporator. The crude product consisted of 28.0
g of a rose-colored oil, which contained .about.89% the desired
product and 11% 1-phenyl-5-(trifluoromethyl)-3-methylpyrazole.
[0321] .sup.1H NMR (DMSO-D.sub.6) 67 2.35 (s,3H), 6.76 (s,1H),
7.6-7.5 (m,5H).
[0322] Step B: Preparation of
1-Phenyl-3-(trifluoromethyl)-1H-pyrazole-5-c- arboxylic acid
[0323] A sample of crude
1-phenyl-3-(trifiuoromethyl)-5-methylpyrazole (.about.89%, 50.0 g,
0.221 mole) was mixed with water (400 mL) and cetyl
trimethylammonium chloride (4.00 g, 0.011 mole). The mixture was
heated to 95.degree. C. Potassium permanganate was added in 10
equal portions, spaced at .about.8 minute intervals. The reaction
mass was maintained at 95-100.degree. C. during this period. After
the last portion was added, the mixture was held for .about.15
minutes at 95-100.degree. C., whereupon the purple, permanganate
color had been discharged. The reaction mass was filtered while hot
(.about.75.degree. C.) through a 1 cm thick bed of Celite.RTM. on a
150 ml, coarse, glass frit. The filter cake was washed with warm
(.about.50.degree. C.) water (3.times.100 mL). The combined
filtrate and washings were extracted with ether (2.times.100 mL) to
remove a small amount of yellow, water-insoluble material. The
aqueous layer was purged with nitrogen to remove residual ether.
The clear, colorless alkaline solution was acidified by adding
concentrated hydrochloric acid dropwise until the pH reached
.about.1.3 (28 g, 0.28 mole). Gas evolution was vigorous during the
first two-thirds of the addition. The product was collected via
filtration, washed with water (3.times.40 mL), then dried overnight
at 55.degree. C. in vacuo. The product consisted of 11.7 g of a
white, crystalline powder, which was essentially pure based upon
.sup.1H NMR.
[0324] .sup.1H NMR (CDCl.sub.3) 67 7.33 (s,1H), 7.4-7.5 (m,5H).
[0325] Step C: Preparation of
1-Phenyl-3-(trifluoromethyl)-1H-pyrazole-5-c- arbonyl chloride
[0326] A sample of crude
1-phenyl-3-(trifluoromethyl)pyrazole-5-carboxylic acid (4.13 g,
16.1 mmol) was dissolved in methylene chloride (45 mL). The
solution was treated with oxalyl chloride (1.80 mL, 20.6 mmol),
followed by N,N-dimethylformamide (0.010 mL, 0.13 mmol).
Off-gassing began shortly after adding the N,N-dimethylformamide
catalyst. The reaction mixture was stirred for .about.20 minutes
under ambient conditions, then was heated to reflux for a period of
35 minutes. Volatiles were removed by stripping the reaction
mixture on a rotary evaporator at a bath temperature of 55.degree.
C. The product consisted of 4.43 g of a light-yellow oil. The only
impurity observed by .sup.1H NMR was N,N-dimethylformamide.
[0327] .sup.1H NMR (CDCl.sub.3) 67 7.40 (m,1H), 7.42 (s,1H),
7.50-7.53 (m,4H).
[0328] Step D: Preparation of
N-[2-Methyl-6-[[(1-methylethyl)amino]carbony-
l]phenyl]-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide
[0329] A sample of 3-methylisatoic anhydride (0.30 g, 1.7 mmol)
partially dissolved in pyridine (4.0 mL) was treated with
1-phenyl-3-(trifluorometh- ylpyrazole)-5-carboxyl chloride (0.55 g,
1.9 mmol). The mixture was heated to .about.95.degree. C. for a
period of 2 hours. The resulting orange solution was cooled to
29.degree. C., then was treated with isopropylamine (1.00 g, 16.9
mmol). The reaction mass self-heated to 39.degree. C. It was
further heated to 55.degree. C. for a period of 30 minutes,
whereupon much precipitate formed. The reaction mass was dissolved
in methylene chloride (150 mL). The solution was washed with
aqueous acid (5 mL conc. HCl in 45 mL water), then with aqueous
base (2 g sodium carbonate in 50 mL water). The organic layer was
dried over MgSO.sub.4, filtered, then concentrated on a rotary
evaporator. Upon reduction to .about.4 mL, product crystals had
formed. The slurry was diluted with .about.10 mL of ether,
whereupon more product precipitated. The product was isolated by
filtration, washed with ether (2.times.10 mL), then washed with
water (2.times.50 mL). The wet cake was dried for 30 minutes at
70.degree. C. in vacuo. The product consisted of 0.52 g of an
off-white powder melting at 260-262.degree. C.
[0330] .sup.1H NMR (DMSO-D.sub.6) .delta. 1.07 (d,6H), 2.21 (s,3H),
4.02 (octet,1H), 7.2-7.4 (m,3H), 7.45-7.6 (m,6H), 8.10 (d,1H),
10.31 (s,1H).
EXAMPLE 7
[0331] Step A: Preparation of
3-Trifluoromethyl-2-[3-(trifluoromethyl)-1H--
pyrazol-1-yl]pyridine
[0332] A mixture of 2-chloro-3-trifluoromethylpyridine (3.62 g., 21
mmol), 3-trifiluoromethylpyrazole (2.7 g., 20 mmol ), and potassium
carbonate (6.0 g., 43 mmol ) were heated at 100.degree. C. for 18
h. The cooled reaction mixture was added to ice/water (100 mL). The
mixture was extracted twice with ether (100 mL) and the combined
ether extracts were washed twice with water (100 mL). The organic
layer was dried with magnesium sulfate and concentrated to an oil.
Chromatography on silica gel with hexanes:ethyl acetate 8:1 to 4:1
as eluent gave the title compound (3.5 g) as an oil. .sup.1H NMR
(CDCl.sub.3) .delta. 6.75 (m,1H), 7.5 (m,1H), 8.2 (m,2H), 8.7
(m,1H).
[0333] Step B: Preparation of
3-(Trifluoromethyl)-1-[3-(trifluoromethyl)-2-
-pyridinyl]-1H-pyrazole-5-carboxylic acid
[0334] A mixture of the title compound of Example 5, Step A (3.4 g,
13 mmol) was dissolved in tetrahydrofuran (30 mL) and cooled to
-70.degree. C. Lithium diisopropylamide (2N in
heptane/tetrahydrofuran, (Aldrich) 9.5 mL, 19 mmol) was added and
the resulting dark mixture was stirred for 10 minutes. Dry carbon
dioxide was bubbled through the mixture for 15 minutes. The mixture
was allowed to warm to 23.degree. C. and treated with water (50 mL)
and 1 N sodium hydroxide (10 mL). The aqueous mixture was extracted
with ether (100 mL) and then ethyl acetate (100 mL). The aqueous
layer was acidified with 6N hydrochloric acid to pH 1-2 and
extracted twice with dichloromethane. The organic layer was dried
with magnesium sulfate and concentrated to give the title compound
(1.5 g). .sup.1H NMR (CDCl.sub.3) .delta. 7.6 (m,1H), 7.95 (m,1H),
8.56 (m,1H)), 8.9 (m,1H), 14.2 (br,1H)
[0335] Step C: Preparation of
N-[2-Methyl-6-[[(1-methylethyl)amino]carbony-
l]phenyl]-3-(trifluoromethyl)-1-[3-(trifluoromethyl)-2-pyridinyl]-1-1H-pyr-
azole-5-carboxamide
[0336] A mixture of the title compound of Example 5, Step B (0.54
g, 1.1 mmol), the title compound from Example 1, Step B (0.44 g,
2.4 mmol) and bop chloride (bis(2-oxo-oxazolidinyl)phosphinyl
chloride, 0.54 g, 2.1 mmol) in acetonitrile (13 mL) was treated
with triethylamine (0.9 mL). The mixture was shaken in a closed
scintillation vial for 18 h. The reaction was partitioned between
ethyl acetate (100 mL) and 1N hydrochloric acid. The ethyl acetate
layer was washed successively with 1N hydrochloric acid (50 mL), 1N
sodium hydroxide (50 mL) and saturated sodium chloride solution (50
mL). The organic layer was dried over magnesium sulfate and
concentrated. The residue was subjected to column chromatography on
silica gel with hexanes/ethyl acetate (5:1 to 3:1) as eluent. The
title compound (0.43 g) was isolated as a white solid. m.p.
227-230.degree. C. .sup.1H NMR (CDCl.sub.3) .delta. 1.2 (m, 6H),
4.15 (m, 1H), 5.9 (br d,1H), 7.1 (m,1H), 7.2 (m,2H), 7.4 (s,1H),
7.6 (m,1H), 8.15 (m,1H), 8.74 (m,1H), 10.4 (br,1H).
[0337] By the procedures described herein together with methods
known in the art, the following compounds of Tables 1 to 17 can be
prepared. The following abbreviations are used in the Tables: t is
tertiary, s is secondary, n is normal, i is iso, c is cyclo, Me is
methyl, Et is ethyl, Pr is propyl, i-Pr is isopropyl, t-Bu is tert
butyl, Ph is phenyl, OMe is methoxy, OEt is ethoxy, SMe is
methylthio, SEt is ethylthio, CN is cyano, NO.sub.2 is nitro, TMS
is trimethylsilyl, S(O)Me is methylsulfinyl, and S(O).sub.2Me is
methylsulfonyl.
1TABLE 1 40 R.sup.4 R.sup.5 and/or R.sup.6 Me 2-CF.sub.3 Me
2-OCF.sub.3 Me 2-OCF.sub.2H Me 2-OCF.sub.2CF.sub.2H Me
2-OCH.sub.2CF.sub.3 Me 2-SCF.sub.3 Me 2-SOCF.sub.3 Me
2-SO.sub.2CF.sub.3 Me 2-SCF.sub.2H Me 2-SOCF.sub.2H Me
2-SO.sub.2CF.sub.2H Cl 2-CF.sub.3 Cl 2-OCF.sub.3 Cl 2-OCF.sub.2H Cl
2-OCF.sub.2CF.sub.2H Cl 2-OCH.sub.2CF.sub.3 Cl 2-SCF.sub.3 Cl
2-SOCF.sub.3 Cl 2-SO.sub.2CF.sub.3 Cl 2-SCF.sub.2H Cl 2-SOCF.sub.2H
Cl 2-SO.sub.2CF.sub.2H F 2-CF.sub.3 F 2-OCF.sub.3 F 2-OCF.sub.2H F
2-OCF.sub.2CF.sub.2H F 2-OCH.sub.2CF.sub.3 F 2-SCF.sub.3 F
2-SOCF.sub.3 F 2-SO.sub.2CF.sub.3 F 2-SCF.sub.2H F 2-SOCF.sub.2H F
2-SO.sub.2CF.sub.2H Br 2-CF.sub.3 Br 2-OCF.sub.3 Br 2-OCF.sub.2H Br
2-OCF.sub.2CF.sub.2H Br 2-OCH.sub.2CF.sub.3 Br 2-SCF.sub.3 Br
2-SOCF.sub.3 Br 2-SO.sub.2CF.sub.3 Br 2-SCF.sub.2H Br 2-SOCF.sub.2H
Br 2-SO.sub.2CF.sub.2H I 2-CF.sub.3 I 2-OCF.sub.3 I 2-OCF.sub.2H I
2-OCF.sub.2CF.sub.2H I 2-OCH.sub.2CF.sub.3 I 2-SCF.sub.3 I
2-SOCF.sub.3 I 2-SO.sub.2CF.sub.3 I 2-SCF.sub.2H I 2-SOCF.sub.2H I
2-SO.sub.2CF.sub.2H OMe 2-CF.sub.3 OMe 2-OCF.sub.3 OMe 2-OCF.sub.2H
OMe 2-OCF.sub.2CF.sub.2H OMe 2-OCH.sub.2CF.sub.3 OMe 2-SCF.sub.3
OMe 2-SOCF.sub.3 OMe 2-SO.sub.2CF.sub.3 OMe 2-SCF.sub.2H OMe
2-SOCF.sub.2H OMe 2-SO.sub.2CF.sub.2H CF.sub.3 2-CF.sub.3 CF.sub.3
2-OCF.sub.3 CF.sub.3 2-OCF.sub.2H CF.sub.3 2-OCF.sub.2CF.sub.2H
CF.sub.3 2-OCH.sub.2CF.sub.3 CF.sub.3 2-SCF.sub.3 CF.sub.3
2-SOCF.sub.3 CF.sub.3 2-SO.sub.2CF.sub.3 CF.sub.3 2-SCF.sub.2H
CF.sub.3 2-SOCF.sub.2H CF.sub.3 2-SO.sub.2CF.sub.2H OCF.sub.2H
2-CF.sub.3 OCF.sub.2H 2-OCF.sub.3 OCF.sub.2H 2-OCF.sub.2H
OCF.sub.2H 2-OCF.sub.2CF.sub.2H OCF.sub.2H 2-OCH.sub.2CF.sub.3
OCF.sub.2H 2-SCF.sub.3 OCF.sub.2H 2-SOCF.sub.3 OCF.sub.2H
2-SO.sub.2CF.sub.3 OCF.sub.2H 2-SCF.sub.2H OCF.sub.2H 2-SOCF.sub.2H
OCF.sub.2H 2-SO.sub.2CF.sub.2H Me 2-Me-4-CF.sub.3 Me
2-Me-4-OCF.sub.3 Me 2-Me-4-OCF.sub.2H Me 2-Me-4-OCH.sub.2CF.sub.3
Me 2-Me-4-SCF.sub.3 Me 2-Me-4-SOCF.sub.3 Me 2-Me-4-SO.sub.2CF.sub.3
Me 2-Me-4-SCF.sub.2H Me 2-Me-4-SOCF.sub.2H Me
2-Me-4-SO.sub.2CF.sub.2H Br 2-Me-4-CF.sub.3 Br 2-Me-4-OCF.sub.3 Br
2-Me-4-OCF.sub.2H Br 2-Me-4-OCH.sub.2CF.sub.3 Br 2-Me-4-SCF.sub.3
Br 2-Me-4-SOCF.sub.3 Br 2-Me-4-SO.sub.2CF.sub.3 Br
2-Me-4-SCF.sub.2H Br 2-Me-4-SOCF.sub.2H Br 2-Me-4-SO.sub.2CF.sub.2H
CF.sub.3 2-Me-4-CF.sub.3 CF.sub.3 2-Me-4-OCF.sub.3 CF.sub.3
2-Me-4-OCF.sub.2H CF.sub.3 2-Me-4-OCH.sub.2CF.sub.3 CF.sub.3
2-Me-4-SCF.sub.3 CF.sub.3 2-Me-4-SOCF.sub.3 CF.sub.3
2-Me-4-SO.sub.2CF.sub.3 CF.sub.3 2-Me-4-SCF.sub.2H CF.sub.3
2-Me-4-SOCF.sub.2H CF.sub.3 2-Me-4-SO.sub.2CF.sub.2H Me 3-CF.sub.3
Me 3-OCF.sub.3 Me 3-OCF.sub.2H Me 3-OCF.sub.2CF.sub.2H Me
3-OCH.sub.2CF.sub.3 Me 3-SCF.sub.3 Me 3-SOCF.sub.3 Me
3-SO.sub.2CF.sub.3 Me 3-SCF.sub.2H Me 3-SOCF.sub.2H Me
3-SO.sub.2CF.sub.2H Cl 3-CF.sub.3 Cl 3-OCF.sub.3 Cl 3-OCF.sub.2H Cl
3-OCF.sub.2CF.sub.2H Cl 3-OCH.sub.2CF.sub.3 Cl 3-SCF.sub.3 Cl
3-SOCF.sub.3 Cl 3-SO.sub.2CF.sub.3 Cl 3-SCF.sub.2H Cl 3-SOCF.sub.2H
Cl 3-SO.sub.2CF.sub.2H F 3-CF.sub.3 F 3-OCF.sub.3 F 3-OCF.sub.2H F
3-OCF.sub.2CF.sub.2H F 3-OCH.sub.2CF.sub.3 F 3-SCF.sub.3 F
3-SOCF.sub.3 F 3-SO.sub.2CF.sub.3 F 3-SCF.sub.2H F 3-SOCF.sub.2H F
3-SO.sub.2CF.sub.2H Br 3-CF.sub.3 Br 3-OCF.sub.3 Br 3-OCF.sub.2H Br
3-OCF.sub.2CF.sub.2H Br 3-OCH.sub.2CF.sub.3 Br 3-SCF.sub.3 Br
3-SOCF.sub.3 Br 3-SO.sub.2CF.sub.3 Br 3-SCF.sub.2H Br 3-SOCF.sub.2H
Br 3-SO.sub.2CF.sub.2H I 3-CF.sub.3 I 3-OCF.sub.3 I 3-OCF.sub.2H I
3-OCF.sub.2CF.sub.2H I 3-OCH.sub.2CF.sub.3 I 3-SCF.sub.3 I
3-SOCF.sub.3 I 3-SO.sub.2CF.sub.3 I 3-SCF.sub.2H I 3-SOCF.sub.2H I
3-SO.sub.2CF.sub.2H OMe 3-CF.sub.3 OMe 3-OCF.sub.3 OMe 3-OCF.sub.2H
OMe 3-OCF.sub.2CF.sub.2H OMe 3-OCH.sub.2CF.sub.3 OMe 3-SCF.sub.3
OMe 3-SOCF.sub.3 OMe 3-SO.sub.2CF.sub.3 OMe 3-SCF.sub.2H OMe
3-SOCF.sub.2H OMe 3-SO.sub.2CF.sub.2H CF.sub.3 3-CF.sub.3 CF.sub.3
3-OCF.sub.3 CF.sub.3 3-OCF.sub.2H CF.sub.3 3-OCF.sub.2CF.sub.2H
CF.sub.3 3-OCH.sub.2CF.sub.3 CF.sub.3 3-SCF.sub.3 CF.sub.3
3-SOCF.sub.3 CF.sub.3 3-SO.sub.2CF.sub.3 CF.sub.3 3-SCF.sub.2H
CF.sub.3 3-SOCF.sub.2H CF.sub.3 3-SO.sub.2CF.sub.2H OCF.sub.2H
3-CF.sub.3 OCF.sub.2H 3-OCF.sub.3 OCF.sub.2H 3-OCF.sub.2H
OCF.sub.2H 3-OCF.sub.2CF.sub.2H OCF.sub.2H 3-OCH.sub.2CF.sub.3
OCF.sub.2H 3-SCF.sub.3 OCF.sub.2H 3-SOCF.sub.3 OCF.sub.2H
3-SO.sub.2CF.sub.3 OCF.sub.2H 3-SCF.sub.2H OCF.sub.2H 3-SOCF.sub.2H
OCF.sub.2H 3-SO.sub.2CF.sub.2H F 2-Me-4-CF.sub.3 F 2-Me-4-OCF.sub.3
F 2-Me-4-OCF.sub.2H F 2-Me-4-OCH.sub.2CF.sub.3 F 2-Me-4-SCF.sub.3 F
2-Me-4-SOCF.sub.3 F 2-Me-4-SO.sub.2CF.sub.3 F 2-Me-4-SCF.sub.2H F
2-Me-4-SOCF.sub.2H F 2-Me-4-SO.sub.2CF.sub.2H I 2-Me-4-CF.sub.3 I
2-Me-4-OCF.sub.3 I 2-Me-4-OCF.sub.2H I 2-Me-4-OCH.sub.2CF.sub.3 I
2-Me-4-SCF.sub.3 I 2-Me-4-SOCF.sub.3 I 2-Me-4-SO.sub.2CF.sub.3 I
2-Me-4-SCF.sub.2H I 2-Me-4-SOCF.sub.2H I 2-Me-4-SO.sub.2CF.sub.2H
NO.sub.2 2-Me-4-CF.sub.3 NO.sub.2 2-Me-4-OCF.sub.3 NO.sub.2
2-Me-4-OCF.sub.2H NO.sub.2 2-Me-4-OCH.sub.2CF.sub.3 NO.sub.2
2-Me-4-SCF.sub.3 NO.sub.2 2-Me-4-SOCF.sub.3 NO.sub.2
2-Me-4-SO.sub.2CF.sub.3 NO.sub.2 2-Me-4-SCF.sub.2H NO.sub.2
2-Me-4-SOCF.sub.2H NO.sub.2 2-Me-4-SO.sub.2CF.sub.2H Me 4-CF.sub.3
Me 4-OCF.sub.3 Me 4-OCF.sub.2H Me 4-OCF.sub.2CF.sub.2H Me
4-OCH.sub.2CF.sub.3 Me 4-SCF.sub.3 Me 4-SOCF.sub.3 Me
4-SO.sub.2CF.sub.3 Me 4-SCF.sub.2H Me 4-SOCF.sub.2H Me
4-SO.sub.2CF.sub.2H Cl 4-CF.sub.3 Cl 4-OCF.sub.3 Cl 4-OCF.sub.2H Cl
4-OCF.sub.2CF.sub.2H Cl 4-OCH.sub.2CF.sub.3 Cl 4-SCF.sub.3 Cl
4-SOCF.sub.3 Cl 4-SO.sub.2CF.sub.3 Cl 4-SCF.sub.2H Cl 4-SOCF.sub.2H
Cl 4-SO.sub.2CF.sub.2H F 4-CF.sub.3 F 4-OCF.sub.3 F 4-OCF.sub.2H F
4-OCF.sub.2CF.sub.2H F 4-OCH.sub.2CF.sub.3 F 4-SCF.sub.3 F
4-SOCF.sub.3 F 4-SO.sub.2CF.sub.3 F 4-SCF.sub.2H F 4-SOCF.sub.2H F
4-SO.sub.2CF.sub.2H Br 4-CF.sub.3 Br 4-OCF.sub.3 Br 4-OCF.sub.2H Br
4-OCF.sub.2CF.sub.2H Br 4-OCH.sub.2CF.sub.3 Br 4-SCF.sub.3 Br
4-SOCF.sub.3 Br 4-SO.sub.2CF.sub.3 Br 4-SCF.sub.2H Br 4-SOCF.sub.2H
Br 4-SO.sub.2CF.sub.2H I 4-CF.sub.3 I 4-OCF.sub.3 I 4-OCF.sub.2H I
4-OCF.sub.2CF.sub.2H I 4-OCH.sub.2CF.sub.3 I 4-SCF.sub.3 I
4-SOCF.sub.3 I 4-SO.sub.2CF.sub.3 I 4-SCF.sub.2H I 4-SOCF.sub.2H I
4-SO.sub.2CF.sub.2H OMe 4-CF.sub.3 OMe 4-OCF.sub.3 OMe 4-OCF.sub.2H
OMe 4-OCF.sub.2CF.sub.2H OMe 4-OCH.sub.2CF.sub.3 OMe 4-SCF.sub.3
OMe 4-SOCF.sub.3 OMe 4-SO.sub.2CF.sub.3 OMe 4-SCF.sub.2H OMe
4-SOCF.sub.2H OMe 4-SO.sub.2CF.sub.2H CF.sub.3 4-CF.sub.3 CF.sub.3
4-OCF.sub.3 CF.sub.3 4-OCF.sub.2H CF.sub.3 4-OCF.sub.2CF.sub.2H
CF.sub.3 4-OCH.sub.2CF.sub.3 CF.sub.3 4-SCF.sub.3 CF.sub.3
4-SOCF.sub.3 CF.sub.3 4-SO.sub.2CF.sub.3 CF.sub.3 4-SCF.sub.2H
CF.sub.3 4-SOCF.sub.2H CF.sub.3 4-SO.sub.2CF.sub.2H OCF.sub.2H
4-CF.sub.3 OCF.sub.2H 4-OCF.sub.3 OCF.sub.2H 4-OCF.sub.2H
OCF.sub.2H 4-OCF.sub.2CF.sub.2H OCF.sub.2H 4-OCH.sub.2CF.sub.3
OCF.sub.2H 4-SCF.sub.3 OCF.sub.2H 4-SOCF.sub.3 OCF.sub.2H
4-SO.sub.2CF.sub.3 OCF.sub.2H 4-SCF.sub.2H OCF.sub.2H 4-SOCF.sub.2H
OCF.sub.2H 4-SO.sub.2CF.sub.2H Cl 2-Me-4-CF.sub.3 Cl
2-Me-4-OCF.sub.3 Cl 2-Me-4-OCF.sub.2H Cl 2-Me-4-OCH.sub.2CF.sub.3
Cl 2-Me-4-SCF.sub.3 Cl 2-Me-4-SOCF.sub.3 Cl 2-Me-4-SO.sub.2CF.sub.3
Cl 2-Me-4-SCF.sub.2H Cl 2-Me-4-SOCF.sub.2H Cl
2-Me-4-SO.sub.2CF.sub.2H OMe 2-Me-4-CF.sub.3 OMe 2-Me-4-OCF.sub.3
OMe 2-Me-4-OCF.sub.2H OMe 2-Me-4-OCH.sub.2CF.sub.3 OMe
2-Me-4-SCF.sub.3 OMe 2-Me-4-SOCF.sub.3 OMe 2-Me-4-SO.sub.2CF.sub.3
OMe 2-Me-4-SCF.sub.2H OMe 2-Me-4-SOCF.sub.2H OMe
2-Me-4-SO.sub.2CF.sub.2H SMe 2-Me-4-CF.sub.3 SMe 2-Me-4-OCF.sub.3
SMe 2-Me-4-OCF.sub.2H SMe 2-Me-4-OCH.sub.2CF.sub.3 SMe
2-Me-4-SCF.sub.3 SMe 2-Me-4-SOCF.sub.3 SMe 2-Me-4-SO.sub.2CF.sub.3
SMe 2-Me-4-SCF.sub.2H SMe 2-Me-4-SOCF.sub.2H SMe
2-Me-4-SO.sub.2CF.sub.2H
[0338]
2TABLE 2 41 R.sup.4 R.sup.5 and/or R.sup.6 Me 2-CF.sub.3 Me
2-OCF.sub.3 Me 2-OCF.sub.2H Me 2-OCF.sub.2CF.sub.2H Me
2-OCH.sub.2CF.sub.3 Me 2-SCF.sub.3 Me 2-SOCF.sub.3 Me
2-SO.sub.2CF.sub.3 Me 2-SCF.sub.2H Me 2-SOCF.sub.2H Me
2-SO.sub.2CF.sub.2H Cl 2-CF.sub.3 Cl 2-OCF.sub.3 Cl 2-OCF.sub.2H Cl
2-OCF.sub.2CF.sub.2H Cl 2-OCH.sub.2CF.sub.3 Cl 2-SCF.sub.3 Cl
2-SOCF.sub.3 Cl 2-SO.sub.2CF.sub.3 Cl 2-SCF.sub.2H Cl 2-SOCF.sub.2H
Cl 2-SO.sub.2CF.sub.2H F 2-CF.sub.3 F 2-OCF.sub.3 F 2-OCF.sub.2H F
2-OCF.sub.2CF.sub.2H F 2-OCH.sub.2CF.sub.3 F 2-SCF.sub.3 F
2-SOCF.sub.3 F 2-SO.sub.2CF.sub.3 F 2-SCF.sub.2H F 2-SOCF.sub.2H F
2-SO.sub.2CF.sub.2H Br 2-CF.sub.3 Br 2-OCF.sub.3 Br 2-OCF.sub.2H Br
2-OCF.sub.2CF.sub.2H Br 2-OCH.sub.2CF.sub.3 Br 2-SCF.sub.3 Br
2-SOCF.sub.3 Br 2-SO.sub.2CF.sub.3 Br 2-SCF.sub.2H Br 2-SOCF.sub.2H
Br 2-SO.sub.2CF.sub.2H I 2-CF.sub.3 I 2-OCF.sub.3 I 2-OCF.sub.2H I
2-OCF.sub.2CF.sub.2H I 2-OCH.sub.2CF.sub.3 I 2-SCF.sub.3 I
2-SOCF.sub.3 I 2-SO.sub.2CF.sub.3 I 2-SCF.sub.2H I 2-SOCF.sub.2H I
2-SO.sub.2CF.sub.2H OMe 2-CF.sub.3 OMe 2-OCF.sub.3 OMe 2-OCF.sub.2H
OMe 2-OCF.sub.2CF.sub.2H OMe 2-OCH.sub.2CF.sub.3 OMe 2-SCF.sub.3
OMe 2-SOCF.sub.3 OMe 2-SO.sub.2CF.sub.3 OMe 2-SCF.sub.2H OMe
2-SOCF.sub.2H OMe 2-SO.sub.2CF.sub.2H CF.sub.3 2-CF.sub.3 CF.sub.3
2-OCF CF.sub.3 2-OCF.sub.2H CF.sub.3 2-OCF.sub.2CF.sub.2H CF.sub.3
2-OCH.sub.2CF.sub.3 CF.sub.3 2-SCF.sub.3 CF.sub.3 2-SOCF.sub.3
CF.sub.3 2-SO.sub.2CF.sub.3 CF.sub.3 2-SCF.sub.2H CF.sub.3
2-SOCF.sub.2H CF.sub.3 2-SO.sub.2CF.sub.2H OCF.sub.2H 2-CF.sub.3
OCF.sub.2H 2-OCF.sub.3 OCF.sub.2H 2-OCF.sub.2H OCF.sub.2H
2-OCF.sub.2CF.sub.2H OCF.sub.2H 2-OCH.sub.2CF.sub.3 OCF.sub.2H
2-SCF.sub.3 OCF.sub.2H 2-SOCF.sub.3 OCF.sub.2H 2-SO.sub.2CF.sub.3
OCF.sub.2H 2-SCF.sub.2H OCF.sub.2H 2-SOCF.sub.2H OCF.sub.2H
2-SO.sub.2CF.sub.2H Me 2-Me-4-CF.sub.3 Me 2-Me-4-OCF.sub.3 Me
2-Me-4-OCF.sub.2H Me 2-Me-4-OCH.sub.2CF.sub.3 Me 2-Me-4-SCF.sub.3
Me 2-Me-4-SOCF.sub.3 Me 2-Me-4-SO.sub.2CF.sub.3 Me
2-Me-4-SCF.sub.2H Me 2-Me-4-SOCF.sub.2H Me 2-Me-4-SO.sub.2CF.sub.2H
Br 2-Me-4-CF.sub.3 Br 2-Me-4-OCF.sub.3 Br 2-Me-4-OCF.sub.2H Br
2-Me-4-OCH.sub.2CF.sub.3 Br 2-Me-4-SCF.sub.3 Br 2-Me-4-SOCF.sub.3
Br 2-Me-4-SO.sub.2CF.sub.3 Br 2-Me-4-SCF.sub.2H Br
2-Me-4-SOCF.sub.2H Br 2-Me-4-SO.sub.2CF.sub.2H CF.sub.3
2-Me-4-CF.sub.3 CF.sub.3 2-Me-4-OCF.sub.3 CF.sub.3
2-Me-4-OCF.sub.2H CF.sub.3 2-Me-4-OCH.sub.2CF.sub.3 CF.sub.3
2-Me-4-SCF.sub.3 CF.sub.3 2-Me-4-SOCF.sub.3 CF.sub.3
2-Me-4-SO.sub.2CF.sub.3 CF.sub.3 2-Me-4-SCF.sub.2H CF.sub.3
2-Me-4-SOCF.sub.2H CF.sub.3 2-Me-4-SO.sub.2CF.sub.2H Me 3-CF.sub.3
Me 3-OCF.sub.3 Me 3-OCF.sub.2H Me 3-OCF.sub.2CF.sub.2H Me
3-OCH.sub.2CF.sub.3 Me 3-SCF.sub.3 Me 3-SOCF.sub.3 Me
3-SO.sub.2CF.sub.3 Me 3-SCF.sub.2H Me 3-SOCF.sub.2H Me
3-SO.sub.2CF.sub.2H Cl 3-CF.sub.3 Cl 3-OCF.sub.3 Cl 3-OCF.sub.2H Cl
3-OCF.sub.2CF.sub.2H Cl 3-OCH.sub.2CF.sub.3 Cl 3-SCF.sub.3 Cl
3-SOCF.sub.3 Cl 3-SO.sub.2CF.sub.3 Cl 3-SCF.sub.2H Cl 3-SOCF.sub.2H
Cl 3-SO.sub.2CF.sub.2H F 3-CF.sub.3 F 3-OCF.sub.3 F 3-OCF.sub.2H F
3-OCF.sub.2CF.sub.2H F 3-OCH.sub.2CF.sub.3 F 3-SCF.sub.3 F
3-SOCF.sub.3 F 3-SO.sub.2CF.sub.3 F 3-SCF.sub.2H F 3-SOCF.sub.2H F
3-SO.sub.2CF.sub.2H Br 3-CF.sub.3 Br 3-OCF.sub.3 Br 3-OCF.sub.2H Br
3-OCF.sub.2CF.sub.2H Br 3-OCH.sub.2CF.sub.3 Br 3-SCF.sub.3 Br
3-SOCF.sub.3 Br 3-SO.sub.2CF.sub.3 Br 3-SCF.sub.2H Br 3-SOCF.sub.2H
Br 3-SO.sub.2CF.sub.2H I 3-CF.sub.3 I 3-OCF.sub.3 I 3-OCF.sub.2H I
3-OCF.sub.2CF.sub.2H I 3-OCH.sub.2CF.sub.3 I 3-SCF.sub.3 I
3-SOCF.sub.3 I 3-SO.sub.2CF.sub.3 I 3-SCF.sub.2H I 3-SOCF.sub.2H I
3-SO.sub.2CF.sub.2H OMe 3-CF.sub.3 OMe 3-OCF.sub.3 OMe 3-OCF.sub.2H
OMe 3-OCF.sub.2CF.sub.2H OMe 3-OCH.sub.2CF.sub.3 OMe 3-SCF.sub.3
OMe 3-SOCF.sub.3 OMe 3-SO.sub.2CF.sub.3 OMe 3-SCF.sub.2H OMe
3-SOCF.sub.2H OMe 3-SO.sub.2CF.sub.2H CF.sub.3 3-CF.sub.3 CF.sub.3
3-OCF.sub.3 CF.sub.3 3-OCF.sub.2H CF.sub.3 3-OCF.sub.2CF.sub.2H
CF.sub.3 3-OCH.sub.2CF.sub.3 CF.sub.3 3-SCF.sub.3 CF.sub.3
3-SOCF.sub.3 CF.sub.3 3-SO.sub.2CF.sub.3 CF.sub.3 3-SCF.sub.2H
CF.sub.3 3-SOCF.sub.2H CF.sub.3 3-SO.sub.2CF.sub.2H OCF.sub.2H
3-CF.sub.3 OCF.sub.2H 3-OCF.sub.3 OCF.sub.2H 3-OCF.sub.2H
OCF.sub.2H 3-OCF.sub.2CF.sub.2H OCF.sub.2H 3-OCH.sub.2CF.sub.3
OCF.sub.2H 3-SCF.sub.3 OCF.sub.2H 3-SOCF.sub.3 OCF.sub.2H
3-SO.sub.2CF.sub.3 OCF.sub.2H 3-SCF.sub.2H OCF.sub.2H 3-SOCF.sub.2H
OCF.sub.2H 3-SO.sub.2CF.sub.2H F 2-Me-4-CF.sub.3 F 2-Me-4-OCF.sub.3
F 2-Me-4-OCF.sub.2H F 2-Me-4-OCH.sub.2CF.sub.3 F 2-Me-4-SCF.sub.3 F
2-Me-4-SOCF.sub.3 F 2-Me-4-SO.sub.2CF.sub.3 F 2-Me-4-SCF.sub.2H F
2-Me-4-SOCF.sub.2H F 2-Me-4-SO.sub.2CF.sub.2H I 2-Me-4-Cl.sub.3 I
2-Me-4-OCF.sub.3 I 2-Me-4-OCF.sub.2H I 2-Me-4-OCH.sub.2CF.sub.3 I
2-Me-4-SCF.sub.3 I 2-Me-4-SOCF.sub.3 I 2-Me-4-SO.sub.2CF.sub.3 I
2-Me-4-SCF.sub.2H I 2-Me-4-SOCF.sub.2H I 2-Me-4-SO.sub.2CF.sub.2H
NO.sub.2 2-Me-4-CF.sub.3 NO.sub.2 2-Me-4-OCF.sub.3 NO.sub.2
2-Me-4-OCF.sub.2H NO.sub.2 2-Me-4-OCH.sub.2CF.sub.3 NO.sub.2
2-Me-4-SCF.sub.3 NO.sub.2 2-Me-4-SOCF.sub.3 NO.sub.2
2-Me-4-SO.sub.2CF.sub.3 NO.sub.2 2-Me-4-SCF.sub.2H NO.sub.2
2-Me-4-SOCF.sub.2H NO.sub.2 2-Me-4-SO.sub.2CF.sub.2H Me 4-CF.sub.3
Me 4-OCF.sub.3 Me 4-OCF.sub.2H Me 4-OCF.sub.2CF.sub.2H Me
4-OCH.sub.2CF.sub.3 Me 4-SCF.sub.3 Me 4-SOCF.sub.3 Me
4-SO.sub.2CF.sub.3 Me 4-SCF.sub.2H Me 4-SOCF.sub.2H Me
4-SO.sub.2CF.sub.2H Cl 4-CF.sub.3 Cl 4-OCF.sub.3 Cl 4-OCF.sub.2H Cl
4-OCF.sub.2CF.sub.2H Cl 4-OCH.sub.2CF.sub.3 Cl 4-SCF.sub.3 Cl
4-SOCF.sub.3 Cl 4-SO.sub.2CF.sub.3 Cl 4-SCF.sub.2H Cl 4-SOCF.sub.2H
Cl 4-SO.sub.2CF.sub.2H F 4-CF.sub.3 F 4-OCF.sub.3 F 4-OCF.sub.2H F
4-OCF.sub.2CF.sub.2H F 4-OCH.sub.2CF.sub.3 F 4-SCF.sub.3 F
4-SOCF.sub.3 F 4-SO.sub.2CF.sub.3 F 4-SCF.sub.2H F 4-SOCF.sub.2H F
4-SO.sub.2CF.sub.2H Br 4-CF.sub.3 Br 4-OCF.sub.3 Br 4-OCF.sub.2H Br
4-OCF.sub.2CF.sub.2H Br 4-OCH.sub.2CF.sub.3 Br 4-SCF.sub.3 Br
4-SOCF.sub.3 Br 4-SO.sub.2CF.sub.3 Br 4-SCF.sub.2H Br 4-SOCF.sub.2H
Br 4-SO.sub.2CF.sub.2H I 4-CF.sub.3 I 4-OCF.sub.3 I 4-OCF.sub.2H I
4-OCF.sub.2CF.sub.2H I 4-OCH.sub.2CF.sub.3 I 4-SCF.sub.3 I
4-SOCF.sub.3 I 4-SO.sub.2CF.sub.3 I 4-SCF.sub.2H I 4-SOCF.sub.2H I
4-SO.sub.2CF.sub.2H OMe 4-CF.sub.3 OMe 4-OCF.sub.3 OMe 4-OCF.sub.2H
OMe 4-OCF.sub.2CF.sub.2H OMe 4-OCH.sub.2CF.sub.3 OMe 4-SCF.sub.3
OMe 4-SOCF.sub.3 OMe 4-SO.sub.2CF.sub.3 OMe 4-SCF.sub.2H OMe
4-SOCF.sub.2H OMe 4-SO.sub.2CF.sub.2H CF.sub.3 4-CF.sub.3 CF.sub.3
4-OCF.sub.3 CF.sub.3 4-OCF.sub.2H CF.sub.3 4-OCF.sub.2CF.sub.2H
CF.sub.3 4-OCH.sub.2CF.sub.3 CF.sub.3 4-SCF.sub.3 CF.sub.3
4-SOCF.sub.3 CF.sub.3 4-SO.sub.2CF.sub.3 CF.sub.3 4-SCF.sub.2H
CF.sub.3 4-SOCF.sub.2H CF.sub.3 4-SO.sub.2CF.sub.2H OCF.sub.2H
4-CF.sub.3 OCF.sub.2H 4-OCF.sub.3 OCF.sub.2H 4-OCF.sub.2H
OCF.sub.2H 4-OCF.sub.2CF.sub.2H OCF.sub.2H 4-OCH.sub.2CF.sub.3
OCF.sub.2H 4-SCF.sub.3 OCF.sub.2H 4-SOCF.sub.3 OCF.sub.2H
4-SO.sub.2CF.sub.3 OCF.sub.2H 4-SCF.sub.2H OCF.sub.2H 4-SOCF.sub.2H
OCF.sub.2H 4-SO.sub.2CF.sub.2H Cl 2-Me-4-CF.sub.3 Cl
2-Me-4-OCF.sub.3 Cl 2-Me-4-OCF.sub.2H Cl 2-Me-4-OCH.sub.2CF.sub.3
Cl 2-Me-4-SCF.sub.3 Cl 2-Me-4-SOCF.sub.3 Cl 2-Me-4-SO.sub.2CF.sub.3
Cl 2-Me-4-SCF.sub.2H Cl 2-Me-4-SOCF.sub.2H Cl
2-Me-4-SO.sub.2CF.sub.2H OMe 2-Me-4-CF.sub.3 OMe 2-Me-4-OCF.sub.3
OMe 2-Me-4-OCF.sub.2H OMe 2-Me-4-OCH.sub.2CF.sub.3 OMe
2-Me-4-SCF.sub.3 OMe 2-Me-4-SOCF.sub.3 OMe 2-Me-4-SO.sub.2CF.sub.3
OMe 2-Me-4-SCF.sub.2H OMe 2-Me-4-SOCF.sub.2H OMe
2-Me-4-SO.sub.2CF.sub.2H SMe 2-Me-4-CF.sub.3 SMe 2-Me-4-OCF.sub.3
SMe 2-Me-4-OCF.sub.2H SMe 2-Me-4-OCH.sub.2CF.sub.3 SMe
2-Me-4-SCF.sub.3 SMe 2-Me-4-SOCF.sub.3 SMe 2-Me-4-SO.sub.2CF.sub.3
SMe 2-Me-4-SCF.sub.2H SMe 2-Me-4-SOCF.sub.2H SMe
2-Me-4-SO.sub.2CF.sub.2H
[0339]
3TABLE 3 42 R.sup.4 R.sup.5 and/or R.sup.6 Me 2-CF.sub.3 Me
2-OCF.sub.3 Me 2-OCF.sub.2H Me 2-OCF.sub.2CF.sub.2H Me
2-OCH.sub.2CF.sub.3 Me 2-SCF.sub.3 Me 2-SOCF.sub.3 Me
2-SO.sub.2CF.sub.3 Me 2-SCF.sub.2H Me 2-SOCF.sub.2H Me
2-SO.sub.2CF.sub.2H Cl 2-CF.sub.3 Cl 2-OCF.sub.3 Cl 2-OCF.sub.2H Cl
2-OCF.sub.2CF.sub.2H Cl 2-OCH.sub.2CF.sub.3 Cl 2-SCF.sub.3 Cl
2-SOCF.sub.3 Cl 2-SO.sub.2CF.sub.3 Cl 2-SCF.sub.2H Cl 2-SOCF.sub.2H
Cl 2-SO.sub.2CF.sub.2H F 2-CF.sub.3 F 2-OCF.sub.3 F 2-OCF.sub.2H F
2-OCF.sub.2CF.sub.2H F 2-OCH.sub.2CF.sub.3 F 2-SCF.sub.3 F
2-SOCF.sub.3 F 2-SO.sub.2CF.sub.3 F 2-SCF.sub.2H F 2-SOCF.sub.2H F
2-SO.sub.2CF.sub.2H Br 2-CF.sub.3 Br 2-OCF.sub.3 Br 2-OCF.sub.2H Br
2-OCF.sub.2CF.sub.2H Br 2-OCH.sub.2CF.sub.3 Br 2-SCF.sub.3 Br
2-SOCF.sub.3 Br 2-SO.sub.2CF.sub.3 Br 2-SCF.sub.2H Br 2-SOCF.sub.2H
Br 2-SO.sub.2CF.sub.2H I 2-CF.sub.3 I 2-OCF.sub.3 I 2-OCF.sub.2H I
2-OCF.sub.2CF.sub.2H I 2-OCH.sub.2CF.sub.3 I 2-SCF.sub.3 I
2-SOCF.sub.3 I 2-SO.sub.2CF.sub.3 I 2-SCF.sub.2H I 2-SOCF.sub.2H I
2-SO.sub.2CF.sub.2H OMe 2-CF.sub.3 OMe 2-OCF.sub.3 OMe 2-OCF.sub.2H
OMe 2-OCF.sub.2CF.sub.2H OMe 2-OCH.sub.2CF.sub.3 OMe 2-SCF.sub.3
OMe 2-SOCF.sub.3 OMe 2-SO.sub.2CF.sub.3 OMe 2-SCF.sub.2H OMe
2-SOCF.sub.2H OMe 2-SO.sub.2CF.sub.2H CF.sub.3 2-CF.sub.3 CF.sub.3
2-OCF.sub.3 CF.sub.3 2-OCF.sub.2H CF.sub.3 2-OCF.sub.2CF.sub.2H
CF.sub.3 2-OCH.sub.2CF.sub.3 CF.sub.3 2-SCF.sub.3 CF.sub.3
2-SOCF.sub.3 CF.sub.3 2-SO.sub.2CF.sub.3 CF.sub.3 2-SCF.sub.2H
CF.sub.3 2-SOCF.sub.2H CF.sub.3 2-SO.sub.2CF.sub.2H OCF.sub.2H
2-CF.sub.3 OCF.sub.2H 2-OCF.sub.3 OCF.sub.2H 2-OCF.sub.2H
OCF.sub.2H 2-OCF.sub.2CF.sub.2H OCF.sub.2H 2-OCH.sub.2CF.sub.3
OCF.sub.2H 2-SCF.sub.3 OCF.sub.2H 2-SOCF.sub.3 OCF.sub.2H
2-SO.sub.2CF.sub.3 OCF.sub.2H 2-SCF.sub.2H OCF.sub.2H 2-SOCF.sub.2H
OCF.sub.2H 2-SO.sub.2CF.sub.2H Me 2-Me-4-CF.sub.3 Me
2-Me-4-OCF.sub.3 Me 2-Me-4-OCF.sub.2H Me 2-Me-4-OCH.sub.2CF.sub.3
Me 2-Me-4-SCF.sub.3 Me 2-Me-4-SOCF.sub.3 Me 2-Me-4-SO.sub.2CF.sub.3
Me 2-Me-4-SCF.sub.2H Me 2-Me-4-SOCF.sub.2H Me
2-Me-4-SO.sub.2CF.sub.2H Br 2-Me-4-CF.sub.3 Br 2-Me-4-OCF.sub.3 Br
2-Me-4-OCF.sub.2H Br 2-Me-4-OCH.sub.2CF.sub.3 Br 2-Me-4-SCF.sub.3
Br 2-Me-4-SOCF.sub.3 Br 2-Me-4-SO.sub.2CF.sub.3 Br
2-Me-4-SCF.sub.2H Br 2-Me-4-SOCF.sub.2H Br 2-Me-4-SO.sub.2CF.sub.2H
CF.sub.3 2-Me-4-CF.sub.3 CF.sub.3 2-Me-4-OCF.sub.3 CF.sub.3
2-Me-4-OCF.sub.2H CF.sub.3 2-Me-4-OCH.sub.2CF.sub.3 CF.sub.3
2-Me-4-SCF.sub.3 CF.sub.3 2-Me-4-SOCF.sub.3 CF.sub.3
2-Me-4-SO.sub.2CF.sub.3 CF.sub.3 2-Me-4-SCF.sub.2H CF.sub.3
2-Me-4-SOCF.sub.2H CF.sub.3 2-Me-4-SO.sub.2CF.sub.2H Me 3-CF.sub.3
Me 3-OCF.sub.3 Me 3-OCF.sub.2H Me 3-OCF.sub.2CF.sub.2H Me
3-OCH.sub.2CF.sub.3 Me 3-SCF.sub.3 Me 3-SOCF.sub.3 Me
3-SO.sub.2CF.sub.3 Me 3-SCF.sub.2H Me 3-SOCF.sub.2H Me
3-SO.sub.2CF.sub.2H Cl 3-CF.sub.3 Cl 3-OCF.sub.3 Cl 3-OCF.sub.2H Cl
3-OCF.sub.2CF.sub.2H Cl 3-OCH.sub.2CF.sub.3 Cl 3-SCF.sub.3 Cl
3-SOCF.sub.3 Cl 3-SO.sub.2CF.sub.3 Cl 3-SCF.sub.2H Cl 3-SOCF.sub.2H
Cl 3-SO.sub.2CF.sub.2H F 3-CF.sub.3 F 3-OCF.sub.3 F 3-OCF.sub.2H F
3-OCF.sub.2CF.sub.2H F 3-OCH.sub.2CF.sub.3 F 3-SCF.sub.3 F
3-SOCF.sub.3 F 3-SO.sub.2CF.sub.3 F 3-SCF.sub.2H F 3-SOCF.sub.2H F
3-SO.sub.2CF.sub.2H Br 3-CF.sub.3 Br 3-OCF.sub.3 Br 3-OCF.sub.2H Br
3-OCF.sub.2CF.sub.2H Br 3-OCH.sub.2CF.sub.3 Br 3-SCF.sub.3 Br
3-SOCF.sub.3 Br 3-SO.sub.2CF.sub.3 Br 3-SCF.sub.2H Br 3-SOCF.sub.2H
Br 3-SO.sub.2CF.sub.2H I 3-CF.sub.3 I 3-OCF.sub.3 I 3-OCF.sub.2H I
3-OCF.sub.2CF.sub.2H I 3-OCH.sub.2CF.sub.3 I 3-SCF.sub.3 I
3-SOCF.sub.3 I 3-SO.sub.2CF.sub.3 I 3-SCF.sub.2H I 3-SOCF.sub.2H I
3-SO.sub.2CF.sub.2H OMe 3-CF.sub.3 OMe 3-OCF.sub.3 OMe 3-OCF.sub.2H
OMe 3-OCF.sub.2CF.sub.2H OMe 3-OCH.sub.2CF.sub.3 OMe 3-SCF.sub.3
OMe 3-SOCF.sub.3 OMe 3-SO.sub.2CF.sub.3 OMe 3-SCF.sub.2H OMe
3-SOCF.sub.2H OMe 3-SO.sub.2CF.sub.2H CF.sub.3 3-CF.sub.3 CF.sub.3
3-OCF.sub.3 CF.sub.3 3-OCF.sub.2H CF.sub.3 3-OCF.sub.2CF.sub.2H
CF.sub.3 3-OCH.sub.2CF.sub.3 CF.sub.3 3-SCF.sub.3 CF.sub.3
3-SOCF.sub.3 CF.sub.3 3-SO.sub.2CF.sub.3 CF.sub.3 3-SCF.sub.2H
CF.sub.3 3-SOCF.sub.2H CF.sub.3 3-SO.sub.2CF.sub.2H OCF.sub.2H
3-CF.sub.3 OCF.sub.2H 3-OCF.sub.3 OCF.sub.2H 3-OCF.sub.2H
OCF.sub.2H 3-OCF.sub.2CF.sub.2H OCF.sub.2H 3-OCH.sub.2CF.sub.3
OCF.sub.2H 3-SCF.sub.3 OCF.sub.2H 3-SOCF.sub.3 OCF.sub.2H
3-SO.sub.2CF.sub.3 OCF.sub.2H 3-SCF.sub.2H OCF.sub.2H 3-SOCF.sub.2H
OCF.sub.2H 3-SO.sub.2CF.sub.2H F 2-Me-4-CF.sub.3 F 2-Me-4-OCF.sub.3
F 2-Me-4-OCF.sub.2H F 2-Me-4-OCH.sub.2CF.sub.3 F 2-Me-4-SCF.sub.3 F
2-Me-4-SOCF.sub.3 F 2-Me-4-SO.sub.2CF.sub.3 F 2-Me-4-SCF.sub.2H F
2-Me-4-SOCF.sub.2H F 2-Me-4-SO.sub.2CF.sub.2H I 2-Me-4-CF.sub.3 I
2-Me-4-OCF.sub.3 I 2-Me-4-OCF.sub.2H I 2-Me-4-OCH.sub.2CF.sub.3 I
2-Me-4-SCF.sub.3 I 2-Me-4-SOCF.sub.3 I 2-Me-4-SO.sub.2CF.sub.3 I
2-Me-4-SCF.sub.2H I 2-Me-4-SOCF.sub.2H I 2-Me-4-SO.sub.2CF.sub.2H
NO.sub.2 2-Me-4-CF.sub.3 NO.sub.2 2-Me-4-OCF.sub.3 NO.sub.2
2-Me-4-OCF.sub.2H NO.sub.2 2-Me-4-OCH.sub.2CF.sub.3 NO.sub.2
2-Me-4-SCF.sub.3 NO.sub.2 2-Me-4-SOCF.sub.3 NO.sub.2
2-Me-4-SO.sub.2CF.sub.3 NO.sub.2 2-Me-4-SCF.sub.2H NO.sub.2
2-Me-4-SOCF.sub.2H NO.sub.2 2-Me-4-SO.sub.2CF.sub.2H Me 4-CF.sub.3
Me 4-OCF.sub.3 Me 4-OCF.sub.2H Me 4-OCF.sub.2CF.sub.2H Me
4-OCH.sub.2CF.sub.3 Me 4-SCF.sub.3 Me 4-SOCF.sub.3 Me
4-SO.sub.2CF.sub.3 Me 4-SCF.sub.2H Me 4-SOCF.sub.2H Me
4-SO.sub.2CF.sub.2H Cl 4-CF.sub.3 Cl 4-OCF.sub.3 Cl 4-OCF.sub.2H Cl
4-OCF.sub.2CF.sub.2H Cl 4-OCH.sub.2CF.sub.3 Cl 4-SCF.sub.3 Cl
4-SOCF.sub.3 Cl 4-SO.sub.2CF.sub.3 Cl 4-SCF.sub.2H Cl 4-SOCF.sub.2H
Cl 4-SO.sub.2CF.sub.2H F 4-CF.sub.3 F 4-OCF.sub.3 F 4-OCF.sub.2H F
4-OCF.sub.2CF.sub.2H F 4-OCH.sub.2CF.sub.3 F 4-SCF.sub.3 F
4-SOCF.sub.3 F 4-SO.sub.2CF.sub.3 F 4-SCF.sub.2H F 4-SOCF.sub.2H F
4-SO.sub.2CF.sub.2H Br 4-CF.sub.3 Br 4-OCF.sub.3 Br 4-OCF.sub.2H Br
4-OCF.sub.2CF.sub.2H Br 4-OCH.sub.2CF.sub.3 Br 4-SCF.sub.3 Br
4-SOCF.sub.3 Br 4-SO.sub.2CF.sub.3 Br 4-SCF.sub.2H Br 4-SOCF.sub.2H
Br 4-SO.sub.2CF.sub.2H I 4-CF.sub.3 I 4-OCF.sub.3 I 4-OCF.sub.2H I
4-OCF.sub.2CF.sub.2H I 4-OCH.sub.2CF.sub.3 I 4-SCF.sub.3 I
4-SOCF.sub.3 I 4-SO.sub.2CF.sub.3 I 4-SCF.sub.2H I 4-SOCF.sub.2H I
4-SO.sub.2CF.sub.2H OMe 4-CF.sub.3 OMe 4-OCF.sub.3 OMe 4-OCF.sub.2H
OMe 4-OCF.sub.2CF.sub.2H OMe 4-OCH.sub.2CF.sub.3 OMe 4-SCF.sub.3
OMe 4-SOCF.sub.3 OMe 4-SO.sub.2CF.sub.3 OMe 4-SCF.sub.2H OMe
4-SOCF.sub.2H OMe 4-SO.sub.2CF.sub.2H CF.sub.3 4-CF.sub.3 CF.sub.3
4-OCF.sub.3 CF.sub.3 4-OCF.sub.2H CF.sub.3 4-OCF.sub.2CF.sub.2H
CF.sub.3 4-OCH.sub.2CF.sub.3 CF.sub.3 4-SCF.sub.3 CF.sub.3
4-SOCF.sub.3 CF.sub.3 4-SO.sub.2CF.sub.3 CF.sub.3 4-SCF.sub.2H
CF.sub.3 4-SOCF.sub.2H CF.sub.3 4-SO.sub.2CF.sub.2H OCF.sub.2H
4-CF.sub.3 OCF.sub.2H 4-OCF.sub.3 OCF.sub.2H 4-OCF.sub.2H
OCF.sub.2H 4-OCF.sub.2CF.sub.2H OCF.sub.2H 4-OCH.sub.2CF.sub.3
OCF.sub.2H 4-SCF.sub.3 OCF.sub.2H 4-SOCF.sub.3 OCF.sub.2H
4-SO.sub.2CF.sub.3 OCF.sub.2H 4-SCF.sub.2H OCF.sub.2H 4-SOCF.sub.2H
OCF.sub.2H 4-SO.sub.2CF.sub.2H Cl 2-Me-4-CF.sub.3 Cl
2-Me-4-OCF.sub.3 Cl 2-Me-4-OCF.sub.2H Cl 2-Me-4-OCH.sub.2CF.sub.3
Cl 2-Me-4-SCF.sub.3 Cl 2-Me-4-SOCF.sub.3 Cl 2-Me-4-SO.sub.2CF.sub.3
Cl 2-Me-4-SCF.sub.2H Cl 2-Me-4-SOCF.sub.2H Cl
2-Me-4-SO.sub.2CF.sub.2H OMe 2-Me-4-CF.sub.3 OMe 2-Me-4-OCF.sub.3
OMe 2-Me-4-OCF.sub.2H OMe 2-Me-4-OCH.sub.2CF.sub.3 OMe
2-Me-4-SCF.sub.3 OMe 2-Me-4-SOCF.sub.3 OMe 2-Me-4-SO.sub.2CF.sub.3
OMe 2-Me-4-SCF.sub.2H OMe 2-Me-4-SOCF.sub.2H OMe
2-Me-4-SO.sub.2CF.sub.2H SMe 2-Me-4-CF.sub.3 SMe 2-Me-4-OCF.sub.3
SMe 2-Me-4-OCF.sub.2H SMe 2-Me-4-OCH.sub.2CF.sub.3 SMe
2-Me-4-SCF.sub.3 SMe 2-Me-4-SOCF.sub.3 SMe 2-Me-4-SO.sub.2CF.sub.3
SMe 2-Me-4-SCF.sub.2H SMe 2-Me-4-SOCF.sub.2H SMe
2-Me-4-SO.sub.2CF.sub.2H
[0340]
4TABLE 4 43 R.sup.4 R.sup.5 and/or R.sup.6 Me 2-CF.sub.3 Me
2-OCF.sub.3 Me 2-OCF.sub.2H Me 2-OCF.sub.2CF.sub.2H Me
2-OCH.sub.2CF.sub.3 Me 2-SCF.sub.3 Me 2-SOCF.sub.3 Me
2-SO.sub.2CF.sub.3 Me 2-SCF.sub.2H Me 2-SOCF.sub.2H Me
2-SO.sub.2CF.sub.2H Cl 2-CF.sub.3 Cl 2-OCF.sub.3 Cl 2-OCF.sub.2H Cl
2-OCF.sub.2CF.sub.2H Cl 2-OCH.sub.2CF.sub.3 Cl 2-SCF.sub.3 Cl
2-SOCF.sub.3 Cl 2-SO.sub.2CF.sub.3 Cl 2-SCF.sub.2H Cl 2-SOCF.sub.2H
Cl 2-SO.sub.2CF.sub.2H F 2-CF.sub.3 F 2-OCF.sub.3 F 2-OCF.sub.2H F
2-OCF.sub.2CF.sub.2H F 2-OCH.sub.2CF.sub.3 F 2-SCF.sub.3 F
2-SOCF.sub.3 F 2-SO.sub.2CF.sub.3 F 2-SCF.sub.2H F 2-SOCF.sub.2H F
2-SO.sub.2CF.sub.2H Br 2-CF.sub.3 Br 2-OCF.sub.3 Br 2-OCF.sub.2H Br
2-OCF.sub.2CF.sub.2H Br 2-OCH.sub.2CF.sub.3 Br 2-SCF.sub.3 Br
2-SOCF.sub.3 Br 2-SO.sub.2CF.sub.3 Br 2-SCF.sub.2H Br 2-SOCF.sub.2H
Br 2-SO.sub.2CF.sub.2H I 2-CF.sub.3 I 2-OCF.sub.3 I 2-OCF.sub.2H I
2-OCF.sub.2CF.sub.2H I 2-OCH.sub.2CF.sub.3 I 2-SCF.sub.3 I
2-SOCF.sub.3 I 2-SO.sub.2CF.sub.3 I 2-SCF.sub.2H I 2-SOCF.sub.2H I
2-SO.sub.2CF.sub.2H OMe 2-CF.sub.3 OMe 2-OCF.sub.3 OMe 2-OCF.sub.2H
OMe 2-OCF.sub.2CF.sub.2H OMe 2-OCH.sub.2CF.sub.3 OMe 2-SCF.sub.3
OMe 2-SOCF.sub.3 OMe 2-SO.sub.2CF.sub.3 OMe 2-SCF.sub.2H OMe
2-SOCF.sub.2H OMe 2-SO.sub.2CF.sub.2H CF.sub.3 2-CF.sub.3 CF.sub.3
2-OCF.sub.3 CF.sub.3 2-OCF.sub.2H CF.sub.3 2-OCF.sub.2CF.sub.2H
CF.sub.3 2-OCH.sub.2CF.sub.3 CF.sub.3 2-SCF.sub.3 CF.sub.3
2-SOCF.sub.3 CF.sub.3 2-SO.sub.2CF.sub.3 CF.sub.3 2-SCF.sub.2H
CF.sub.3 2-SOCF.sub.2H CF.sub.3 2-SO.sub.2CF.sub.2H OCF.sub.2H
2-CF.sub.3 OCF.sub.2H 2-OCF.sub.3 OCF.sub.2H 2-OCF.sub.2H
OCF.sub.2H 2-OCF.sub.2CF.sub.2H OCF.sub.2H 2-OCH.sub.2CF.sub.3
OCF.sub.2H 2-SCF.sub.3 OCF.sub.2H 2-SOCF.sub.3 OCF.sub.2H
2-SO.sub.2CF.sub.3 OCF.sub.2H 2-SCF.sub.2H OCF.sub.2H 2-SOCF.sub.2H
OCF.sub.2H 2-SO.sub.2CF.sub.2H Me 2-Me-4-CF.sub.3 Me
2-Me-4-OCF.sub.3 Me 2-Me-4-OCF.sub.2H Me 2-Me-4-OCH.sub.2CF.sub.3
Me 2-Me-4-SCF.sub.3 Me 2-Me-4-SOCF.sub.3 Me 2-Me-4-SO.sub.2CF.sub.3
Me 2-Me-4-SCF.sub.2H Me 2-Me-4-SOCF.sub.2H Me
2-Me-4-SO.sub.2CF.sub.2H Br 2-Me-4-CF.sub.3 Br 2-Me-4-OCF.sub.3 Br
2-Me-4-OCF.sub.2H Br 2-Me-4-OCH.sub.2CF.sub.3 Br 2-Me-4-SCF.sub.3
Br 2-Me-4-SOCF.sub.3 Br 2-Me-4-SO.sub.2CF.sub.3 Br
2-Me-4-SCF.sub.2H Br 2-Me-4-SOCF.sub.2H Br 2-Me-4-SO.sub.2CF.sub.2H
CF.sub.3 2-Me-4-CF.sub.3 CF.sub.3 2-Me-4-OCF.sub.3 CF.sub.3
2-Me-4-OCF.sub.2H CF.sub.3 2-Me-4-OCH.sub.2CF.sub.3 CF.sub.3
2-Me-4-SCF.sub.3 CF.sub.3 2-Me-4-SOCF.sub.3 CF.sub.3
2-Me-4-SO.sub.2CF.sub.3 CF.sub.3 2-Me-4-SCF.sub.2H CF.sub.3
2-Me-4-SOCF.sub.2H CF.sub.3 2-Me-4-SO.sub.2CF.sub.2H Me 3-CF.sub.3
Me 3-OCF.sub.3 Me 3-OCF.sub.2H Me 3-OCF.sub.2CF.sub.2H Me
3-OCH.sub.2CF.sub.3 Me 3-SCF.sub.3 Me 3-SOCF.sub.3 Me
3-SO.sub.2CF.sub.3 Me 3-SCF.sub.2H Me 3-SOCF.sub.2H Me
3-SO.sub.2CF.sub.2H Cl 3-CF.sub.3 Cl 3-OCF.sub.3 Cl 3-OCF.sub.2H Cl
3-OCF.sub.2CF.sub.2H Cl 3-OCH.sub.2CF.sub.3 Cl 3-SCF.sub.3 Cl
3-SOCF.sub.3 Cl 3-SO.sub.2CF.sub.3 Cl 3-SCF.sub.2H Cl 3-SOCF.sub.2H
Cl 3-SO.sub.2CF.sub.2H F 3-CF.sub.3 F 3-OCF.sub.3 F 3-OCF.sub.2H F
3-OCF.sub.2CF.sub.2H F 3-OCH.sub.2CF.sub.3 F 3-SCF.sub.3 F
3-SOCF.sub.3 F 3-SO.sub.2CF.sub.3 F 3-SCF.sub.2H F 3-SOCF.sub.2H F
3-SO.sub.2CF.sub.2H Br 3-CF.sub.3 Br 3-OCF.sub.3 Br 3-OCF.sub.2H Br
3-OCF.sub.2CF.sub.2H Br 3-OCH.sub.2CF.sub.3 Br 3-SCF.sub.3 Br
3-SOCF.sub.3 Br 3-SO.sub.2CF.sub.3 Br 3-SCF.sub.2H Br 3-SOCF.sub.2H
Br 3-SO.sub.2CF.sub.2H I 3-CF.sub.3 I 3-OCF.sub.3 I 3-OCF.sub.2H I
3-OCF.sub.2CF.sub.2H I 3-OCH.sub.2CF.sub.3 I 3-SCF.sub.3 I
3-SOCF.sub.3 I 3-SO.sub.2CF.sub.3 I 3-SCF.sub.2H I 3-SOCF.sub.2H I
3-SO.sub.2CF.sub.2H OMe 3-CF.sub.3 OMe 3-OCF.sub.3 OMe 3-OCF.sub.2H
OMe 3-OCF.sub.2CF.sub.2H OMe 3-OCH.sub.2CF.sub.3 OMe 3-SCF.sub.3
OMe 3-SOCF.sub.3 OMe 3-SO.sub.2CF.sub.3 OMe 3-SCF.sub.2H OMe
3-SOCF.sub.2H OMe 3-SO.sub.2CF.sub.2H CF.sub.3 3-CF.sub.3 CF.sub.3
3-OCF.sub.3 CF.sub.3 3-OCF.sub.2H CF.sub.3 3-OCF.sub.2CF.sub.2H
CF.sub.3 3-OCH.sub.2CF.sub.3 CF.sub.3 3-SCF.sub.3 CF.sub.3
3-SOCF.sub.3 CF.sub.3 3-SO.sub.2CF.sub.3 CF.sub.3 3-SCF.sub.2H
CF.sub.3 3-SOCF.sub.2H CF.sub.3 3-SO.sub.2CF.sub.2H OCF.sub.2H
3-CF.sub.3 OCF.sub.2H 3-OCF.sub.3 OCF.sub.2H 3-OCF.sub.2H
OCF.sub.2H 3-OCF.sub.2CF.sub.2H OCF.sub.2H 3-OCH.sub.2CF.sub.3
OCF.sub.2H 3-SCF.sub.3 OCF.sub.2H 3-SOCF.sub.3 OCF.sub.2H
3-SO.sub.2CF.sub.3 OCF.sub.2H 3-SCF.sub.2H OCF.sub.2H 3-SOCF.sub.2H
OCF.sub.2H 3-SO.sub.2CF.sub.2H F 2-Me-4-CF.sub.3 F 2-Me-4-OCF.sub.3
F 2-Me-4-OCF.sub.2H F 2-Me-4-OCH.sub.2CF.sub.3 F 2-Me-4-SCF.sub.3 F
2-Me-4-SOCF.sub.3 F 2-Me-4-SO.sub.2CF.sub.3 F 2-Me-4-SCF.sub.2H F
2-Me-4-SOCF.sub.2H F 2-Me-4-SO.sub.2CF.sub.2H I 2-Me-4-CF.sub.3 I
2-Me-4-OCF.sub.3 I 2-Me-4-OCF.sub.2H I 2-Me-4-OCH.sub.2CF.sub.3 I
2-Me-4-SCF.sub.3 I 2-Me-4-SOCF.sub.3 I 2-Me-4-SO.sub.2CF.sub.3 I
2-Me-4-SCF.sub.2H I 2-Me-4-SOCF.sub.2H I 2-Me-4-SO.sub.2CF.sub.2H
NO.sub.2 2-Me-4-CF.sub.3 NO.sub.2 2-Me-4-OCF.sub.3 NO.sub.2
2-Me-4-OCF.sub.2H NO.sub.2 2-Me-4-OCH.sub.2CF.sub.3 NO.sub.2
2-Me-4-SCF.sub.3 NO.sub.2 2-Me-4-SOCF.sub.3 NO.sub.2
2-Me-4-SO.sub.2CF.sub.3 NO.sub.2 2-Me-4-SCF.sub.2H NO.sub.2
2-Me-4-SOCF.sub.2H NO.sub.2 2-Me-4-SO.sub.2CF.sub.2H Me 4-CF.sub.3
Me 4-OCF.sub.3 Me 4-OCF.sub.2H Me 4-OCF.sub.2CF.sub.2H Me
4-OCH.sub.2CF.sub.3 Me 4-SCF.sub.3 Me 4-SOCF.sub.3 Me
4-SO.sub.2CF.sub.3 Me 4-SCF.sub.2H Me 4-SOCF.sub.2H Me
4-SO.sub.2CF.sub.2H Cl 4-CF.sub.3 Cl 4-OCF.sub.3 Cl 4-OCF.sub.2H Cl
4-OCF.sub.2CF.sub.2H Cl 4-OCH.sub.2CF.sub.3 Cl 4-SCF.sub.3 Cl
4-SOCF.sub.3 Cl 4-SO.sub.2CF.sub.3 Cl 4-SCF.sub.2H Cl 4-SOCF.sub.2H
Cl 4-SO.sub.2CF.sub.2H F 4-CF.sub.3 F 4-OCF.sub.3 F 4-OCF.sub.2H F
4-OCF.sub.2CF.sub.2H F 4-OCH.sub.2CF.sub.3 F 4-SCF.sub.3 F
4-SOCF.sub.3 F 4-SO.sub.2CF.sub.3 F 4-SCF.sub.2H F 4-SOCF.sub.2H F
4-SO.sub.2CF.sub.2H Br 4-CF.sub.3 Br 4-OCF.sub.3 Br 4-OCF.sub.2H Br
4-OCF.sub.2CF.sub.2H Br 4-OCH.sub.2CF.sub.3 Br 4-SCF.sub.3 Br
4-SOCF.sub.3 Br 4-SO.sub.2CF.sub.3 Br 4-SCF.sub.2H Br 4-SOCF.sub.2H
Br 4-SO.sub.2CF.sub.2H I 4-CF.sub.3 I 4-OCF.sub.3 I 4-OCF.sub.2H I
4-OCF.sub.2CF.sub.2H I 4-OCH.sub.2CF.sub.3 I 4-SCF.sub.3 I
4-SOCF.sub.3 I 4-SO.sub.2CF.sub.3 I 4-SCF.sub.2H I 4-SOCF.sub.2H I
4-SO.sub.2CF.sub.2H OMe 4-CF.sub.3 OMe 4-OCF.sub.3 OMe 4-OCF.sub.2H
OMe 4-OCF.sub.2CF.sub.2H OMe 4-OCH.sub.2CF.sub.3 OMe 4-SCF.sub.3
OMe 4-SOCF.sub.3 OMe 4-SO.sub.2CF.sub.3 OMe 4-SCF.sub.2H OMe
4-SOCF.sub.2H OMe 4-SO.sub.2CF.sub.2H CF.sub.3 4-CF.sub.3 CF.sub.3
4-OCF.sub.3 CF.sub.3 4-OCF.sub.2H CF.sub.3 4-OCF.sub.2CF.sub.2H
CF.sub.3 4-OCH.sub.2CF.sub.3 CF.sub.3 4-SCF.sub.3 CF.sub.3
4-SOCF.sub.3 CF.sub.3 4-SO.sub.2CF.sub.3 CF.sub.3 4-SCF.sub.2H
CF.sub.3 4-SOCF.sub.2H CF.sub.3 4-SO.sub.2CF.sub.2H OCF.sub.2H
4-CF.sub.3 OCF.sub.2H 4-OCF.sub.3 OCF.sub.2H 4-OCF.sub.2H
OCF.sub.2H 4-OCF.sub.2CF.sub.2H OCF.sub.2H 4-OCH.sub.2CF.sub.3
OCF.sub.2H 4-SCF.sub.3 OCF.sub.2H 4-SOCF.sub.3 OCF.sub.2H
4-SO.sub.2CF.sub.3 OCF.sub.2H 4-SCF.sub.2H OCF.sub.2H 4-SOCF.sub.2H
OCF.sub.2H 4-SO.sub.2CF.sub.2H Cl 2-Me-4-CF.sub.3 Cl
2-Me-4-OCF.sub.3 Cl 2-Me-4-OCF.sub.2H Cl 2-Me-4-OCH.sub.2CF.sub.3
Cl 2-Me-4-SCF.sub.3 Cl 2-Me-4-SOCF.sub.3 Cl 2-Me-4-SO.sub.2CF.sub.3
Cl 2-Me-4-SCF.sub.2H Cl 2-Me-4-SOCF.sub.2H Cl
2-Me-4-SO.sub.2CF.sub.2H OMe 2-Me-4-CF.sub.3 OMe 2-Me-4-OCF.sub.3
OMe 2-Me-4-OCF.sub.2H OMe 2-Me-4-OCH.sub.2CF.sub.3 OMe
2-Me-4-SCF.sub.3 OMe 2-Me-4-SOCF.sub.3 OMe 2-Me-4-SO.sub.2CF.sub.3
OMe 2-Me-4-SCF.sub.2H OMe 2-Me-4-SOCF.sub.2H OMe
2-Me-4-SO.sub.2CF.sub.2H SMe 2-Me-4-CF.sub.3 SMe 2-Me-4-OCF.sub.3
SMe 2-Me-4-OCF.sub.2H SMe 2-Me-4-OCH.sub.2CF.sub.3 SMe
2-Me-4-SCF.sub.3 SMe 2-Me-4-SOCF.sub.3 SMe 2-Me-4-SO.sub.2CF.sub.3
SMe 2-Me-4-SCF.sub.2H SMe 2-Me-4-SOCF.sub.2H SMe
2-Me-4-SO.sub.2CF.sub.2H
[0341]
5TABLE 5 44 R.sup.3 R.sup.4 R.sup.7 W X Y Z i-Pr Me CF.sub.3 CMe N
CH CH i-Pr Cl CF.sub.3 CMe N CH CH i-Pr Br CF.sub.3 CMe N CH CH
i-Pr I CF.sub.3 CMe N CH CH i-Pr F CF.sub.3 CMe N CH CH i-Pr H
CF.sub.3 CMe N CH CH i-Pr Et CF.sub.3 CMe N CH CH i-Pr Me CF.sub.3
CMe CH N CH i-Pr Cl CF.sub.3 CMe CH N CH i-Pr Br CF.sub.3 CMe CH N
CH i-Pr I CF.sub.3 CMe CH N CH i-Pr F CF.sub.3 CMe CH N CH i-Pr H
CF.sub.3 CMe CH N CH i-Pr Et CF.sub.3 CMe CH N CH i-Pr Me CF.sub.3
CMe CH CH N i-Pr Cl CF.sub.3 CMe CH CH N i-Pr Br CF.sub.3 CMe CH CH
N i-Pr I CF.sub.3 CMe CH CH N i-Pr F CF.sub.3 CMe CH CH N i-Pr H
CF.sub.3 CMe CH CH N i-Pr Et CF.sub.3 CMe CH CH N i-Pr Me CF.sub.3
CMe N CH N i-Pr Cl CF.sub.3 CMe N CH N i-Pr Br CF.sub.3 CMe N CH N
i-Pr I CF.sub.3 CMe N CH N i-Pr F CF.sub.3 CMe N CH N i-Pr H
CF.sub.3 CMe N CH N i-Pr Et CF.sub.3 CMe N CH N t-Bu Me CF.sub.3
CMe N CH CH t-Bu Cl CF.sub.3 CMe N CH CH t-Bu Br CF.sub.3 CMe N CH
CH t-Bu I CF.sub.3 CMe N CH CH t-Bu F CF.sub.3 CMe N CH CH t-Bu H
CF.sub.3 CMe N CH CH t-Bu Et CF.sub.3 CMe N CH CH t-Bu Me CF.sub.3
CMe CH N CH t-Bu Cl CF.sub.3 CMe CH N CH t-Bu Br CF.sub.3 CMe CH N
CH t-Bu I CF.sub.3 CMe CH N CH t-Bu F CF.sub.3 CMe CH N CH t-Bu H
CF.sub.3 CMe CH N CH t-Bu Et CF.sub.3 CMe CH N CH t-Bu Me CF.sub.3
CMe CH CH N t-Bu Cl CF.sub.3 CMe CH CH N t-Bu Br CF.sub.3 CMe CH CH
N t-Bu I CF.sub.3 CMe CH CH N t-Bu F CF.sub.3 CMe CH CH N t-Bu H
CF.sub.3 CMe CH CH N t-Bu Et CF.sub.3 CMe CH CH N i-Pr Me OCF.sub.3
CMe N CH CH i-Pr Cl OCF.sub.3 CMe N CH CH i-Pr Br OCF.sub.3 CMe N
CH CH i-Pr I OCF.sub.3 CMe N CH CH i-Pr F OCF.sub.3 CMe N CH CH
i-Pr H OCF.sub.3 CMe N CH CH i-Pr Et OCF.sub.3 CMe N CH CH i-Pr Me
CF.sub.3 CH N CH CH i-Pr Cl CF.sub.3 CH N CH CH i-Pr Br CF.sub.3 CH
N CH CH i-Pr I CF.sub.3 CH N CH CH i-Pr F CF.sub.3 CH N CH CH i-Pr
H CF.sub.3 CH N CH CH i-Pr Et CF.sub.3 CH N CH CH i-Pr Me Cl CMe CH
CH N i-Pr Cl Cl CMe CH CH N i-Pr Br Cl CMe CH CH N i-Pr I Cl CMe CH
CH N i-Pr F Cl CMe CH CH N i-Pr H Cl CMe CH CH N i-Pr Et Cl CMe CH
CH N
[0342]
6TABLE 6 45 R.sup.3 R.sup.4 R.sup.7 X Y Z i-Pr Me CF.sub.3 CMe N CH
i-Pr Cl CF.sub.3 CMe N CH i-Pr Br CF.sub.3 CMe N CH i-Pr I CF.sub.3
CMe N CH i-Pr F CF.sub.3 CMe N CH i-Pr H CF.sub.3 CMe N CH i-Pr Et
CF.sub.3 CMe N CH i-Pr Me CF.sub.3 CMe CH N i-Pr Cl CF.sub.3 CMe CH
N i-Pr Br CF.sub.3 CMe CH N i-Pr I CF.sub.3 CMe CH N i-Pr F
CF.sub.3 CMe CH N i-Pr H CF.sub.3 CMe CH N i-Pr Et CF.sub.3 CMe CH
N i-Pr Me CF.sub.3 CMe N N i-Pr Cl CF.sub.3 CMe N N i-Pr Br
CF.sub.3 CMe N N i-Pr I CF.sub.3 CMe N N i-Pr F CF.sub.3 CMe N N
i-Pr H CF.sub.3 CMe N N i-Pr Et CF.sub.3 CMe N N i-Pr Me CF.sub.3
CEt CH N i-Pr Cl CF.sub.3 CEt CH N i-Pr Br CF.sub.3 CEt CH N i-Pr I
CF.sub.3 CEt CH N i-Pr F CF.sub.3 CEt CH N i-Pr H CF.sub.3 CEt CH N
i-Pr Et CF.sub.3 CEt CH N t-Bu Me CF.sub.3 CMe N CH t-Bu Cl
CF.sub.3 CMe N CH t-Bu Br CF.sub.3 CMe N CH t-Bu I CF.sub.3 CMe N
CH t-Bu F CF.sub.3 CMe N CH t-Bu H CF.sub.3 CMe N CH t-Bu Et
CF.sub.3 CMe N CH t-Bu Me CF.sub.3 CMe CH N t-Bu Cl CF.sub.3 CMe CH
N t-Bu Br CF.sub.3 CMe CH N t-Bu I CF.sub.3 CMe CH N t-Bu F
CF.sub.3 CMe CH N t-Bu H CF.sub.3 CMe CH N t-Bu Et CF.sub.3 CMe CH
N t-Bu Me CF.sub.3 CMe N N t-Bu Cl CF.sub.3 CMe N N t-Bu Br
CF.sub.3 CMe N N t-Bu I CF.sub.3 CMe N N t-Bu F CF.sub.3 CMe N N
t-Bu H CF.sub.3 CMe N N t-Bu Et CF.sub.3 CMe N N i-Pr Me OCF.sub.3
CMe CH N i-Pr Cl OCF.sub.3 CMe CH N i-Pr Br OCF.sub.3 CMe CH N i-Pr
I OCF.sub.3 CMe CH N i-Pr F OCF.sub.3 CMe CH N i-Pr H OCF.sub.3 CMe
CH N i-Pr Et OCF.sub.3 CMe CH N i-Pr Me CF.sub.3 CH CH N i-Pr Cl
CF.sub.3 CH CH N i-Pr Br CF.sub.3 CH CH N i-Pr I CF.sub.3 CH CH N
i-Pr F CF.sub.3 CH CH N i-Pr H CF.sub.3 CH CH N i-Pr Et CF.sub.3 CH
CH N i-Pr Me Cl CMe CH N i-Pr Cl Cl CMe CH N i-Pr Br Cl CMe CH N
i-Pr I Cl CMe CH N i-Pr F Cl CMe CH N i-Pr H Cl CMe CH N i-Pr Et Cl
CMe CH N
[0343]
7TABLE 7 46 R.sup.3 R.sup.4 Q X Y Z i-Pr Me S CCF.sub.3 CH CH i-Pr
Cl S CCF.sub.3 CH CH i-Pr Br S CCF.sub.3 CH CH i-Pr I S CCF.sub.3
CH CH i-Pr F S CCF.sub.3 CH CH i-Pr H S CCF.sub.3 CH CH i-Pr Et S
CCF.sub.3 CH CH i-Pr Me S CCF.sub.3 CMe CH i-Pr Cl S CCF.sub.3 CMe
CH i-Pr Br S CCF.sub.3 CMe CH i-Pr I S CCF.sub.3 CMe CH i-Pr F S
CCF.sub.3 CMe CH i-Pr H S CCF.sub.3 CMe CH i-Pr Et S CCF.sub.3 CMe
CH t-Bu Me S CCF.sub.3 CMe CH t-Bu Cl S CCF.sub.3 CMe CH t-Bu Br S
CCF.sub.3 CMe CH t-Bu I S CCF.sub.3 CMe CH t-Bu F S CCF.sub.3 CMe
CH t-Bu H S CCF.sub.3 CMe CH t-Bu Et S CCF.sub.3 CMe CH i-Pr Me S
CCF.sub.3 CMe N i-Pr Cl S CCF.sub.3 CMe N i-Pr Br S CCF.sub.3 CMe N
i-Pr I S CCF.sub.3 CMe N i-Pr F S CCF.sub.3 CMe N i-Pr H S
CCF.sub.3 CMe N i-Pr Et S CCF.sub.3 CMe N i-Pr Me S
COCH.sub.2CF.sub.3 CMe N i-Pr Cl S COCH.sub.2CF.sub.3 CMe N i-Pr Br
S COCH.sub.2CF.sub.3 CMe N i-Pr I S COCH.sub.2CF.sub.3 CMe N i-Pr F
S COCH.sub.2CF.sub.3 CMe N i-Pr H S COCH.sub.2CF.sub.3 CMe N i-Pr
Et S COCH.sub.2CF.sub.3 CMe N i-Pr Me S COCHF.sub.2 CMe N i-Pr Cl S
COCHF.sub.2 CMe N i-Pr Br S COCHF.sub.2 CMe N i-Pr I S COCHF.sub.2
CMe N i-Pr F S COCHF.sub.2 CMe N i-Pr H S COCHF.sub.2 CMe N i-Pr Et
S COCHF.sub.2 CMe N i-Pr Me O CCF.sub.3 CMe N i-Pr Cl O CCF.sub.3
CMe N i-Pr Br O CCF.sub.3 CMe N i-Pr I O CCF.sub.3 CMe N i-Pr F O
CCF.sub.3 CMe N i-Pr H O CCF.sub.3 CMe N i-Pr Et O CCF.sub.3 CMe N
i-Pr Me NMe N CH CCF.sub.3 i-Pr Cl NMe N CH CCF.sub.3 i-Pr Br NMe N
CH CCF.sub.3 i-Pr I NMe N CH CCF.sub.3 i-Pr F NMe N CH CCF.sub.3
i-Pr H NMe N CH CCF.sub.3 i-Pr Et NMe N CH CCF.sub.3 i-Pr Me NEt N
CH CCF.sub.3 i-Pr Cl NEt N CH CCF.sub.3 i-Pr Br NEt N CH CCF.sub.3
i-Pr I NEt N CH CCF.sub.3 i-Pr F NEt N CH CCF.sub.3 i-Pr H NEt N CH
CCF.sub.3 i-Pr Et NEt N CH CCF.sub.3 i-Pr Me NMe N CH
CC.sub.2F.sub.3 i-Pr Cl NMe N CH CC.sub.2F.sub.3 i-Pr Br NMe N CH
CCF.sub.3 i-Pr I NMe N CH CCF.sub.3 i-Pr F NMe N CH CCF.sub.3 i-Pr
H NMe N CH CCF.sub.3 i-Pr Et NMe N CH CCF.sub.3 t-Bu Me NMe N CH
CCF.sub.3 t-Bu Cl NMe N CH CCF.sub.3 t-Bu Br NMe N CH CCF.sub.3
t-Bu I NMe N CH CCF.sub.3 t-Bu F NMe N CH CCF.sub.3 t-Bu H NMe N CH
CCF.sub.3 t-Bu Et NMe N CH CCF.sub.3 i-Pr Me NMe CH N CCF.sub.3
i-Pr Cl NMe CH N CCF.sub.3 i-Pr Br NMe CH N CCF.sub.3 i-Pr I NMe CH
N CCF.sub.3 i-Pr F NMe CH N CCF.sub.3 i-Pr H NMe CH N CCF.sub.3
i-Pr Et NMe CH N CCF.sub.3 i-Pr Me NMe N N CCF.sub.3 i-Pr Cl NMe N
N CCF.sub.3 i-Pr Br NMe N N CCF.sub.3 i-Pr I NMe N N CCF.sub.3 i-Pr
F NMe N N CCF.sub.3 i-Pr H NMe N N CCF.sub.3 i-Pr Et NMe N N
CCF.sub.3
[0344]
8TABLE 8 47 R.sup.3 R.sup.4 Q X Y Z i-Pr Me NCHF.sub.2 CMe N CH
i-Pr Cl NCHF.sub.2 CMe N CH i-Pr Br NCHF.sub.2 CMe N CH i-Pr I
NCHF.sub.2 CMe N CH i-Pr F NCHF.sub.2 CMe N CH i-Pr H NCHF.sub.2
CMe N CH i-Pr Et NCHF.sub.2 CMe N CH i-Pr Me NCHF.sub.2 CH N CMe
i-Pr Cl NCHF.sub.2 CH N CMe i-Pr Br NCHF.sub.2 CH N CMe i-Pr I
NCHF.sub.2 CH N CMe i-Pr F NCHF.sub.2 CH N CMe i-Pr H NCHF.sub.2 CH
N CMe i-Pr Et NCHF.sub.2 CH N CMe i-Pr Me NCF.sub.2CHF.sub.2 CMe N
CH i-Pr Cl NCF.sub.2CHF.sub.2 CMe N CH i-Pr Br NCF.sub.2CHF.sub.2
CMe N CH i-Pr I NCF.sub.2CHF.sub.2 CMe N CH i-Pr F
NCF.sub.2CHF.sub.2 CMe N CH i-Pr H NCF.sub.2CHF.sub.2 CMe N CH i-Pr
Et NCF.sub.2CHF.sub.2 CMe N CH i-Pr Me NCF.sub.2CHF.sub.2 CH N CMe
i-Pr Cl NCF.sub.2CHF.sub.2 CH N CMe i-Pr Br NCF.sub.2CHF.sub.2 CH N
CMe i-Pr I NCF.sub.2CHF.sub.2 CH N CMe i-Pr F NCF.sub.2CHF.sub.2 CH
N CMe i-Pr H NCF.sub.2CHF.sub.2 CH N CMe i-Pr Et NCF.sub.2CHF.sub.2
CH N CMe i-Pr Me NCH.sub.2CF.sub.3 CMe N CH i-Pr Cl
NCH.sub.2CF.sub.3 CMe N CH i-Pr Br NCH.sub.2CF.sub.3 CMe N CH i-Pr
I NCH.sub.2CF.sub.3 CMe N CH i-Pr F NCH.sub.2CF.sub.3 CMe N CH i-Pr
H NCH.sub.2CF.sub.3 CMe N CH i-Pr Et NCH.sub.2CF.sub.3 CMe N CH
i-Pr Me NCH.sub.2CF.sub.3 CH N CMe i-Pr Cl NCH.sub.2CF.sub.3 CH N
CMe i-Pr Br NCH.sub.2CF.sub.3 CH N CMe i-Pr I NCH.sub.2CF.sub.3 CH
N CMe i-Pr F NCH.sub.2CF.sub.3 CH N CMe i-Pr H NCH.sub.2CF.sub.3 CH
N CMe i-Pr Et NCH.sub.2CF.sub.3 CH N CMe i-Pr Me NCF.sub.2CHF.sub.2
N CH CMe i-Pr Cl NCF.sub.2CHF.sub.2 N CH CMe i-Pr Br
NCF.sub.2CHF.sub.2 N CH CMe i-Pr I NCF.sub.2CHF.sub.2 N CH CMe i-Pr
F NCF.sub.2CHF.sub.2 N CH CMe i-Pr H NCF.sub.2CHF.sub.2 N CH CMe
i-Pr Et NCF.sub.2CHF.sub.2 N CH CMe
[0345]
9TABLE 9 48 W X Y Z R.sup.3 R.sup.4 R.sup.7 R.sup.8 CH CH CH CH
i-Pr Me CF.sub.3 Me CH CH CH CH t-Bu Me CF.sub.3 Me CH CH CH CH
i-Pr Cl CF.sub.3 Me CH CH CH CH t-Bu Cl CF.sub.3 Me CH CH CH CH
i-Pr Br CF.sub.3 Me CH CH CH CH t-Bu Br CF.sub.3 Me CH CH CH CH
i-Pr Me Cl Me CH CH CH CH t-Bu Me Cl Me CH CH CH CH i-Pr Cl Cl Me
CH CH CH CH t-Bu Cl Cl Me CH CH CH CH i-Pr Br Cl Me CH CH CH CH
t-Bu Br Cl Me CH CH CH CH i-Pr Me Br Me CH CH CH CH t-Bu Me Br Me
CH CH CH CH i-Pr Cl Br Me CH CH CH CH t-Bu Cl Br Me CH CH CH CH
i-Pr Br Br Me CH CH CH CH t-Bu Br Br Me CH CH CH CH i-Pr Me CN Me
CH CH CH CH t-Bu Me CN Me CH CH CH CH i-Pr Cl CN Me CH CH CH CH
t-Bu Cl CN Me CH CH CH CH i-Pr Br CN Me CH CH CH CH t-Bu Br CN Me
CH CH CH CH i-Pr Me CF.sub.3 F CH CH CH CH t-Bu Me CF.sub.3 F CH CH
CH CH i-Pr Cl CF.sub.3 F CH CH CH CH t-Bu Cl CF.sub.3 F CH CH CH CH
i-Pr Br CF.sub.3 F CH CH CH CH t-Bu Br CF.sub.3 F CH CH CH CH i-Pr
Me Cl F CH CH CH CH t-Bu Me Cl F CH CH CH CH i-Pr Cl Cl F CH CH CH
CH t-Bu Cl Cl F CH CH CH CH i-Pr Br Cl F CH CH CH CH t-Bu Br Cl F
CH CH CH CH i-Pr Me Br F CH CH CH CH t-Bu Me Br F CH CH CH CH i-Pr
Cl Br F CH CH CH CH t-Bu Cl Br F CH CH CH CH i-Pr Br Br F CH CH CH
CH t-Bu Br Br F CH CH CH CH i-Pr Me CN F CH CH CH CH t-Bu Me CN F
CH CH CH CH i-Pr Cl CN F CH CH CH CH t-Bu Cl CN F CH CH CH CH i-Pr
Br CN F CH CH CH CH t-Bu Br CN F CH CH CH CH i-Pr Me CF.sub.3 Cl CH
CH CH CH t-Bu Me CF.sub.3 Cl CH CH CH CH i-Pr Cl CF.sub.3 Cl CH CH
CH CH t-Bu Cl CF.sub.3 Cl CH CH CH CH i-Pr Br CF.sub.3 Cl CH CH CH
CH t-Bu Br CF.sub.3 Cl CH CH CH CH i-Pr Me Cl Cl CH CH CH CH t-Bu
Me Cl Cl CH CH CH CH i-Pr Cl Cl Cl CH CH CH CH t-Bu Cl Cl Cl CH CH
CH CH i-Pr Br Cl Cl CH CH CH CH t-Bu Br Cl Cl CH CH CH CH i-Pr Me
Br Cl CH CH CH CH t-Bu Me Br Cl CH CH CH CH i-Pr Cl Br Cl CH CH CH
CH t-Bu Cl Br Cl CH CH CH CH i-Pr Br Br Cl CH CH CH CH t-Bu Br Br
Cl CH CH CH CH i-Pr Me CN Cl CH CH CH CH t-Bu Me CN Cl CH CH CH CH
i-Pr Cl CN Cl CH CH CH CH t-Bu Cl CN Cl CH CH CH CH i-Pr Br CN Cl
CH CH CH CH t-Bu Br CN Cl CH CH CH CH i-Pr Me CF.sub.3 Br CH CH CH
CH t-Bu Me CF.sub.3 Br CH CH CH CH i-Pr Cl CF.sub.3 Br CH CH CH CH
t-Bu Cl CF.sub.3 Br CH CH CH CH i-Pr Br CF.sub.3 Br CH CH CH CH
t-Bu Br CF.sub.3 Br CH CH CH CH i-Pr Me Cl Br CH CH CH CH t-Bu Me
Cl Br CH CH CH CH i-Pr Cl Cl Br CH CH CH CH t-Bu Cl Cl Br CH CH CH
CH i-Pr Br Cl Br CH CH CH CH t-Bu Br Cl Br CH CH CH CH i-Pr Me Br
Br CH CH CH CH t-Bu Me Br Br CH CH CH CH i-Pr Cl Br Br CH CH CH CH
t-Bu Cl Br Br CH CH CH CH i-Pr Br Br Br CH CH CH CH t-Bu Br Br Br
CH CH CH CH i-Pr Me CN Br CH CH CH CH t-Bu Me CN Br CH CH CH CH
i-Pr Cl CN Br CH CH CH CH t-Bu Cl CN Br CH CH CH CH i-Pr Br CN Br
CH CH CH CH t-Bu Br CN Br CH CH CH CH i-Pr Me CF.sub.3 CN CH CH CH
CH t-Bu Me CF.sub.3 CN CH CH CH CH i-Pr Cl CF.sub.3 CN CH CH CH CH
t-Bu Cl CF.sub.3 CN CH CH CH CH i-Pr Br CF.sub.3 CN CH CH CH CH
t-Bu Br CF.sub.3 CN CH CH CH CH i-Pr Me Cl CN CH CH CH CH t-Bu Me
Cl CN CH CH CH CH i-Pr Cl Cl CN CH CH CH CH t-Bu Cl Cl CN CH CH CH
CH i-Pr Br Cl CN CH CH CH CH t-Bu Br Cl CN CH CH CH CH i-Pr Me Br
CN CH CH CH CH t-Bu Me Br CN CH CH CH CH i-Pr Cl Br CN CH CH CH CH
t-Bu Cl Br CN CH CH CH CH i-Pr Br Br CN CH CH CH CH t-Bu Br Br CN
CH CH CH CH i-Pr Me CN CN CH CH CH CH t-Bu Me CN CN CH CH CH CH
i-Pr Cl CN CN CH CH CH CH t-Bu Cl CN CN CH CH CH CH i-Pr Br CN CN
CH CH CH CH t-Bu Br CN CN CH CH CH N i-Pr Me CF.sub.3 Me CH CH CH N
t-Bu Me CF.sub.3 Me CH CH CH N i-Pr Cl CF.sub.3 Me CH CH CH N t-Bu
Cl CF.sub.3 Me CH CH CH N i-Pr Br CF.sub.3 Me CH CH CH N t-Bu Br
CF.sub.3 Me CH CH CH N i-Pr Me Cl Me CH CH CH N t-Bu Me Cl Me CH CH
CH N i-Pr Cl Cl Me CH CH CH N t-Bu Cl Cl Me CH CH CH N i-Pr Br Cl
Me CH CH CH N t-Bu Br Cl Me CH CH CH N i-Pr Me Br Me CH CH CH N
t-Bu Me Br Me CH CH CH N i-Pr Cl Br Me CH CH CH N t-Bu Cl Br Me CH
CH CH N i-Pr Br Br Me CH CH CH N t-Bu Br Br Me CH CH CH N i-Pr Me
CN Me CH CH CH N i-Bu Me CN Me CH CH CH N i-Pr Cl CN Me CH CH CH N
t-Bu Cl CN Me CH CH CH N i-Pr Br CN Me CH CH CH N t-Bu Br CN Me CH
CH CH N i-Pr Me CF.sub.3 F CH CH CH N t-Bu Me CF.sub.3 F CH CH CH N
i-Pr Cl CF.sub.3 F CH CH CH N t-Bu Cl CF.sub.3 F CH CH CH N i-Pr Br
CF.sub.3 F CH CH CH N t-Bu Br CF.sub.3 F CH CH CH N i-Pr Me Cl F CH
CH CH N t-Bu Me Cl F CH CH CH N i-Pr Cl Cl F CH CH CH N t-Bu Cl Cl
F CH CH CH N i-Pr Br Cl F CH CH CH N t-Bu Br Cl F CH CH CH N i-Pr
Me Br F CH CH CH N t-Bu Me Br F CH CH CH N i-Pr Cl Br F CH CH CH N
t-Bu Cl Br F CH CH CH N i-Pr Br Br F CH CH CH N t-Bu Br Br F CH CH
CH N i-Pr Me CN F CH CH CH N t-Bu Me CN F CH CH CH N i-Pr Cl CN F
CH CH CH N t-Bu Cl CN F CH CH CH N i-Pr Br CN F CH CH CH N t-Bu Br
CN F CH CH CH N i-Pr Me CF.sub.3 Cl CH CH CH N t-Bu Me CF.sub.3 Cl
CH CH CH N i-Pr Cl CF.sub.3 Cl CH CH CH N t-Bu Cl CF.sub.3 Cl CH CH
CH N i-Pr Br CF.sub.3 Cl CH CH CH N t-Bu Br CF.sub.3 Cl CH CH CH N
i-Pr Me Cl Cl CH CH CH N t-Bu Me Cl Cl CH CH CH N i-Pr Cl Cl Cl CH
CH CH N t-Bu Cl Cl Cl CH CH CH N i-Pr Br Cl Cl CH CH CH N t-Bu Br
Cl Cl CH CH CH N i-Pr Me Br Cl CH CH CH N t-Bu Me Br Cl CH CH CH N
i-Pr Cl Br Cl CH CH CH N t-Bu Cl Br Cl CH CH CH N i-Pr Br Br Cl CH
CH CH N t-Bu Br Br Cl CH CH CH N i-Pr Me CN Cl CH CH CH N t-Bu Me
CN Cl CH CH CH N i-Pr Cl CN Cl CH CH CH N t-Bu Cl CN Cl CH CH CH N
i-Pr Br CN Cl CH CH CH N t-Bu Br CN Cl CH CH CH N i-Pr Me CF.sub.3
Br CH CH CH N t-Bu Me CF.sub.3 Br CH CH CH N i-Pr Cl CF.sub.3 Br CH
CH CH N t-Bu Cl CF.sub.3 Br CH CH CH N i-Pr Br CF.sub.3 Br CH CH CH
N t-Bu Br CF.sub.3 Br CH CH CH N i-Pr Me Cl Br CH CH CH N t-Bu Me
Cl Br CH CH CH N i-Pr Cl Cl Br CH CH CH N t-Bu Cl Cl Br CH CH CH N
i-Pr Br Cl Br CH CH CH N t-Bu Br Cl Br CH CH CH N i-Pr Me Br Br CH
CH CH N t-Bu Me Br Br CH CH CH N i-Pr Cl Br Br CH CH CH N t-Bu Cl
Br Br CH CH CH N i-Pr Br Br Br CH CH CH N t-Bu Br Br Br CH CH CH N
i-Pr Me CN Br CH CH CH N t-Bu Me CN Br CH CH CH N i-Pr Cl CN Br CH
CH CH N t-Bu Cl CN Br CH CH CH N i-Pr Br CN Br CH CH CH N t-Bu Br
CN Br CH CH CH N i-Pr Me CF.sub.3 CN CH CH CH N t-Bu Me CF.sub.3 CN
CH CH CH N i-Pr Cl CF.sub.3 CN CH CH CH N t-Bu Cl CF.sub.3 CN CH CH
CH N i-Pr Br CF.sub.3 CN CH CH CH N t-Bu Br CF.sub.3 CN CH CH CH N
i-Pr Me Cl CN CH CH CH N t-Bu Me Cl CN CH CH CH N i-Pr Cl Cl CN CH
CH CH N t-Bu Cl Cl CN CH CH CH N i-Pr Br Cl CN CH CH CH N t-Bu Br
Cl CN CH CH CH N i-Pr Me Br CN CH CH CH N t-Bu Me Br CN CH CH CH N
i-Pr Cl Br CN CH CH CH N t-Bu Cl Br CN CH CH CH N i-Pr Br Br CN CH
CH CH N t-Bu Br Br CN CH CH CH N i-Pr Me CN CN CH CH CH N t-Bu Me
CN CN CH CH CH N i-Pr Cl CN CN CH CH CH N t-Bu Cl CN CN CH CH CH N
i-Pr Br CN CN CH CH CH N t-Bu Br CN CN CH CH CH CH Me Me CF.sub.3 F
CH CH CH CH Et Me CF.sub.3 F CH CH CH CH
CH(CH.sub.3)CH.sub.2OCH.sub.3 Me CF.sub.3 F CH CH CH CH
CH(CH.sub.3)CH.sub.2SCH.sub.3 Me CF.sub.3 F CH CH CH CH propargyl
Me CF.sub.3 F CH CH CH CH Me Me CF.sub.3 Cl CH CH CH CH Et Me
CF.sub.3 Cl CH CH CH CH CH(CH.sub.3)CH.sub.2OCH.sub.3 Me CF.sub.3
Cl CH CH CH CH CH(CH.sub.3)CH.sub.2SCH.sub.3 Me CF.sub.3 Cl CH CH
CH CH propargyl Me CF.sub.3 Cl CH CH CH CH Me Me Br F CH CH CH CH
Et Me Br F CH CH CH CH CH(CH.sub.3)CH.sub.2OCH.sub.3 Me Br F CH CH
CH CH CH(CH.sub.3)CH.sub.2SCH.sub.3 Me Br F CH CH CH CH propargyl
Me Br F CH CH CH CH Me Me Br Cl CH CH CH CH Et Me Br Cl CH CH CH CH
CH(CH.sub.3)CH.sub.2OCH.sub.3 Me Br Cl CH CH CH CH
CH(CH.sub.3)CH.sub.2SCH.sub.3 Me Br Cl CH CH CH CH propargyl Me Br
Cl CH CH CH CH Me Cl CF.sub.3 F CH CH CH CH Et Cl CF.sub.3 F CH CH
CH CH CH(CH.sub.3)CH.sub.2OCH.sub.3 Cl CF.sub.3 F CH CH CH CH
CH(CH.sub.3)CH.sub.2SCH.sub.3 Cl CF.sub.3 F CH CH CH CH propargyl
Cl CF.sub.3 F CH CH CH CH Me Cl CF.sub.3 Cl CH CH CH CH Et Cl
CF.sub.3 Cl CH CH CH CH CH(CH.sub.3)CH.sub.2OCH.sub- .3 Cl CF.sub.3
Cl CH CH CH CH CH(CH.sub.3)CH.sub.2SCH.sub.3 Cl CF.sub.3 Cl CH CH
CH CH propargyl Cl CF.sub.3 Cl CH CH CH CH Me Cl Br F CH CH CH CH
Et Cl Br F CH CH CH CH CH(CH.sub.3)CH.sub.2OCH.sub.3 Cl Br F CH CH
CH CH CH(CH.sub.3)CH.sub.2SCH.sub.3 Cl Br F CH CH CH CH propargyl
Cl Br F CH CH CH CH Me Cl Br Cl CH CH CH CH Et Cl Br Cl CH CH CH CH
CH(CH.sub.3)CH.sub.2OCH.sub.3 Cl Br Cl CH CH CH CH
CH(CH.sub.3)CH.sub.2SCH.sub.3 Cl Br Cl CH CH CH CH propargyl Cl Br
Cl CH CH CH N Me Me CF.sub.3 F CH CH CH N Et Me CF.sub.3 F CH CH CH
N CH(CH.sub.3)CH.sub.2OCH.sub.3 Me CF.sub.3 F CH CH CH N
CH(CH.sub.3)CH.sub.2SCH.sub.3 Me CF.sub.3 F CH CH CH N propargyl Me
CF.sub.3 F CH CH CH N Me Me CF.sub.3 Cl CH CH CH N Et Me CF.sub.3
Cl CH CH CH N CH(CH.sub.3)CH.sub.2OCH.sub.3 Me CF.sub.3 Cl CH CH CH
N CH(CH.sub.3)CH.sub.2SCH.sub.3 Me CF.sub.3 Cl CH CH CH N propargyl
Me CF.sub.3 Cl CH CH CH N Me Me Br F CH CH CH N Et Me Br F CH CH CH
N CH(CH.sub.3)CH.sub.2OCH.- sub.3 Me Br F CH CH CH N
CH(CH.sub.3)CH.sub.2SCH.sub.3 Me Br F CH CH CH N propargyl Me Br F
CH CH CH N Me Me Br Cl CH CH CH N Et Me Br Cl CH CH CH N
CH(CH.sub.3)CH.sub.2OCH.sub.3 Me Br Cl CH CH CH N
CH(CH.sub.3)CH.sub.2SCH.sub.3 Me Br Cl CH CH CH N propargyl Me Br
Cl CH CH CH N Me Cl CF.sub.3 F CH CH CH N Et Cl CF.sub.3 F CH CH CH
N CH(CH.sub.3)CH.sub.2OCH.sub.3 Cl CF.sub.3 F CH CH CH N
CH(CH.sub.3)CH.sub.2SCH.sub.3 Cl CF.sub.3 F CH CH CH N propargyl Cl
CF.sub.3 F CH CH CH N Me Cl CF.sub.3 Cl CH CH CH N Et Cl CF.sub.3
Cl CH CH CH N CH(CH.sub.3)CH.sub.2OCH.sub.3 Cl CF.sub.3 Cl CH CH CH
N CH(CH.sub.3)CH.sub.2SCH.sub.3 Cl CF.sub.3 Cl CH CH CH N propargyl
Cl CF.sub.3 Cl CH CH CH N Me Cl Br F CH CH CH N Et Cl Br F CH CH CH
N CH(CH.sub.3)CH.sub.2OCH.sub.3 Cl Br F CH CH CH N
CH(CH.sub.3)CH.sub.2SCH.sub.3 Cl Br F CH CH CH N propargyl Cl Br F
CH CH CH N Me Cl Br Cl CH CH CH N Et Cl Br Cl CH CH CH N
CH(CH.sub.3)CH.sub.2OCH.sub.3 Cl Br Cl CH CH CH N
CH(CH.sub.3)CH.sub.2SCH.sub.3 Cl Br Cl CH CH CH N propargyl Cl Br
Cl C--Cl CH CH CH i-Pr Me CF.sub.3 Cl C--F CH CH CH i-Pr Me
CF.sub.3 F CH CH CH CH i-Pr Me CF.sub.3 acetylene CH CH CH CH i-Pr
Me CF.sub.3 I CH CH CH CH i-Pr Me CF.sub.3 SO.sub.2Me C--Cl CH CH
CH i-Pr Cl CF.sub.3 Cl C--F CH CH CH i-Pr Cl CF.sub.3 F CH CH CH CH
i-Pr Cl CF.sub.3 acetylene CH CH CH CH i-Pr Cl CF.sub.3 I CH CH CH
CH i-Pr Cl CF.sub.3 SO.sub.2Me C--Cl CH CH CH i-Pr Me Br Cl C--F CH
CH CH i-Pr Me Br F CH CH CH CH i-Pr Me Br acetylene CH CH CH CH
i-Pr Me Br I CH CH CH CH i-Pr Me Br SO.sub.2Me C--Cl CH CH CH i-Pr
Cl Br Cl C--F CH CH CH i-Pr Cl Br F CH CH CH CH i-Pr Cl Br
acetylene CH CH CH CH i-Pr Cl Br I CH CH CH CH i-Pr Cl Br
SO.sub.2Me C--Cl CH CH N i-Pr Me CF.sub.3 Cl C--F CH CH N i-Pr Me
CF.sub.3 F CH CH CH N i-Pr Me CF.sub.3 acetylene CH CH CH N i-Pr Me
CF.sub.3 I CH CH CH N i-Pr Me CF.sub.3 SO.sub.2Me C--Cl CH CH N
i-Pr Cl CF.sub.3 Cl C--F CH CH N i-Pr Cl CF.sub.3 F CH CH CH N i-Pr
Cl CF.sub.3 acetylene CH CH CH N i-Pr Cl CF.sub.3 I CH CH CH N i-Pr
Cl CF.sub.3 SO.sub.2Me C--Cl CH CH N i-Pr Me Br Cl C--F CH CH N
i-Pr Me Br F CH CH CH N i-Pr Me Br acetylene CH CH CH N i-Pr Me Br
I CH CH CH N i-Pr Me Br SO.sub.2Me C--Cl CH CH N i-Pr Cl Br Cl C--F
CH CH N i-Pr Cl Br F CH CH CH N i-Pr Cl Br acetylene CH CH CH N
i-Pr Cl Br I CH CH CH N i-Pr Cl Br SO.sub.2Me CH N CH N i-Pr Me
CF.sub.3 H CH N CH N i-Pr Me CF.sub.3 Me CH N CH N i-Pr Me CF.sub.3
Cl CH N CH N i-Pr Cl CF.sub.3 H CH N CH N i-Pr Cl CF.sub.3 Me CH N
CH N i-Pr Cl CF.sub.3 Cl CH N CH N i-Pr Me CN H CH N CH N i-Pr Me
CN Me CH N CH N i-Pr Me CN Cl CH N CH N i-Pr Cl CN H CH N CH N i-Pr
Cl CN Me CH N CH N i-Pr Cl CN Cl CH N CH N i-Pr Me Br H CH N CH N
i-Pr Me Br Me CH N CH N i-Pr Me Br Cl CH N CH N i-Pr Cl Br H CH N
CH N i-Pr Cl Br Me CH N CH N i-Pr Cl Br Cl CH N CH N t-Bu Me
CF.sub.3 H CH N CH N t-Bu Me CF.sub.3 Me CH N CH N t-Bu Me CF.sub.3
Cl CH N CH N t-Bu Cl CF.sub.3 H CH N CH N t-Bu Cl CF.sub.3 Me CH N
CH N t-Bu Cl CF.sub.3 Cl CH N CH N t-Bu Me CN H CH N CH N t-Bu Me
CN Me CH N CH N t-Bu Me CN Cl CH N CH N t-Bu Cl CN H CH N CH N t-Bu
Cl CN Me CH N CH N t-Bu Cl CN Cl CH N CH N t-Bu Me Br H CH N CH N
t-Bu Me Br Me CH N CH N t-Bu Me Br Cl CH N CH N t-Bu Cl Br H CH N
CH N t-Bu Cl Br Me CH N CH N t-Bu Cl Br Cl CH CH N N i-Pr Me
CF.sub.3 H CH CH N N i-Pr Me CF.sub.3 Me CH CH N N i-Pr Me CF.sub.3
Cl CH CH N N i-Pr Cl CF.sub.3 H CH CH N N i-Pr Cl CF.sub.3 Me CH CH
N N i-Pr Cl CF.sub.3 Cl CH CH N N i-Pr Me CN H CH CH N N i-Pr Me CN
Me CH CH N N i-Pr Me CN Cl CH CH N N i-Pr Cl CN H CH CH N N i-Pr Cl
CN Me CH CH N N i-Pr Cl CN Cl CH CH N N i-Pr Me Br H CH CH N N i-Pr
Me Br Me CH CH N N i-Pr Me Br Cl CH CH N N i-Pr Cl Br H CH CH N N
i-Pr Cl Br Me CH CH N N i-Pr Cl Br Cl CH CH N N i-Pr Me CF.sub.3 H
CH CH N N i-Pr Me CF.sub.3 Me CH CH N N i-Pr Me CF.sub.3 Cl CH CH N
N i-Pr Cl CF.sub.3 H CH CH N N i-Pr Cl CF.sub.3 Me CH CH N N i-Pr
Cl CF.sub.3 Cl CH CH N N i-Pr Me CN H CH CH N N i-Pr Me CN Me CH CH
N N i-Pr Me CN Cl CH CH N N i-Pr Cl CN H CH CH N N i-Pr Cl CN Me CH
CH N N i-Pr Cl CN Cl CH CH N N i-Pr Me Br H CH CH N N i-Pr Me Br Me
CH CH N N i-Pr Me Br Cl CH CH N N i-Pr Cl Br H CH CH N N i-Pr Cl Br
Me CH CH N N i-Pr Cl Br Cl
[0346]
10TABLE 10 49 R.sup.3 R.sup.4 R.sup.7 R.sup.8 R.sup.9 R.sup.10 Me
CF.sub.3 i-Pr Me H H Me CF.sub.3 i-Pr Me H Me Me CF.sub.3 i-Pr Me
Cl H Me CF.sub.3 i-Pr Me Cl Me Me CF.sub.3 i-Pr Me Me Me Cl
CF.sub.3 i-Pr Me H H Cl CF.sub.3 i-Pr Me H Me Cl CF.sub.3 i-Pr Me
Cl H Cl CF.sub.3 i-Pr Me Cl Me Cl CF.sub.3 i-Pr Me Me Me Me
CF.sub.3 t-Bu Me H H Me CF.sub.3 t-Bu Me H Me Me CF.sub.3 t-Bu Me
Cl H Me CF.sub.3 t-Bu Me Cl Me Me CF.sub.3 t-Bu Me Me Me Cl
CF.sub.3 t-Bu Me H H Cl CF.sub.3 t-Bu Me H Me Cl CF.sub.3 t-Bu Me
Cl H Cl CF.sub.3 t-Bu Me Cl Me Cl CF.sub.3 t-Bu Me Me Me
[0347]
11TABLE 11 50 R.sup.3 R.sup.4 R.sup.7 R.sup.8 R.sup.9 R.sup.10 Me
CF.sub.3 i-Pr Me H Me Me CF.sub.3 i-Pr Me Me Me Me CF.sub.3 i-Pr Cl
H Me Me CF.sub.3 i-Pr Cl Me Me Cl CF.sub.3 i-Pr Me H Me Cl CF.sub.3
i-Pr Me Me Me Cl CF.sub.3 i-Pr Cl H Me Cl CF.sub.3 i-Pr Cl Me Me Me
CF.sub.3 t-Bu Me H Me Me CF.sub.3 t-Bu Me Me Me Me CF.sub.3 t-Bu Cl
H Me Me CF.sub.3 t-Bu Cl Me Me Cl CF.sub.3 t-Bu Me H Me Cl CF.sub.3
t-Bu Me Me Me Cl CF.sub.3 t-Bu Cl H Me Cl CF.sub.3 t-Bu Cl Me
Me
[0348]
12TABLE 12 51 W X Y Z R.sup.3 R.sup.4 R.sup.7 R.sup.8 CH CH CH CH
Et Me CF.sub.3 Cl CH CH CH CH i-Pr Me CF.sub.3 Cl CH CH CH CH t-Bu
Me CF.sub.3 Cl CH CH CH CH Et Me CF.sub.3 Br CH CH CH CH i-Pr Me
CF.sub.3 Br CH CH CH CH t-Bu Me CF.sub.3 Br CH CH CH CH Et Me
CF.sub.3 I CH CH CH CH i-Pr Me CF.sub.3 I CH CH CH CH t-Bu Me
CF.sub.3 I CH CH CH CH Et Me CF.sub.3 F CH CH CH CH i-Pr Me
CF.sub.3 F CH CH CH CH t-Bu Me CF.sub.3 F CH CH CH CH Et Me
CF.sub.3 Me CH CH CH CH i-Pr Me CF.sub.3 Me CH CH CH CH t-Bu Me
CF.sub.3 Me CH CH CH CH Et Me CF.sub.3 CF.sub.3 CH CH CH CH i-Pr Me
CF.sub.3 CF.sub.3 CH CH CH CH t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CH
Et Me CF.sub.3 OMe CH CH CH CH i-Pr Me CF.sub.3 OMe CH CH CH CH
t-Bu Me CF.sub.3 OMe CH CH CH CH Et Me CF.sub.3 CN CH CH CH CH i-Pr
Me CF.sub.3 CN CH CH CH CH t-Bu Me CF.sub.3 CN CH CH CH CH Et Cl
CF.sub.3 Cl CH CH CH CH i-Pr Cl CF.sub.3 Cl CH CH CH CH t-Bu Cl
CF.sub.3 Cl CH CH CH CH Et Cl CF.sub.3 Br CH CH CH CH i-Pr Cl
CF.sub.3 Br CH CH CH CH t-Bu Cl CF.sub.3 Br CH CH CH CH Et Cl
CF.sub.3 I CH CH CH CH i-Pr Cl CF.sub.3 I CH CH CH CH t-Bu Cl
CF.sub.3 I CH CH CH CH Et Cl CF.sub.3 F CH CH CH CH i-Pr Cl
CF.sub.3 F CH CH CH CH t-Bu Cl CF.sub.3 F CH CH CH CH Et Cl
CF.sub.3 Me CH CH CH CH i-Pr Cl CF.sub.3 Me CH CH CH CH t-Bu Cl
CF.sub.3 Me CH CH CH CH Et Cl CF.sub.3 CF.sub.3 CH CH CH CH i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH CH t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CH
Et Cl CF.sub.3 OMe CH CH CH CH i-Pr Cl CF.sub.3 OMe CH CH CH CH
t-Bu Cl CF.sub.3 OMe CH CH CH CH Et Cl CF.sub.3 CN CH CH CH CH i-Pr
Cl CF.sub.3 CN CH CH CH CH t-Bu Cl CF.sub.3 CN CH CH CH N Et Me
CF.sub.3 Cl CH CH CH N i-Pr Me CF.sub.3 Cl CH CH CH N t-Bu Me
CF.sub.3 Cl CH CH CH N Et Me CF.sub.3 Br CH CH CH N i-Pr Me
CF.sub.3 Br CH CH CH N t-Bu Me CF.sub.3 Br CH CH CH N Et Me
CF.sub.3 I CH CH CH N i-Pr Me CF.sub.3 I CH CH CH N t-Bu Me
CF.sub.3 I CH CH CH N Et Me CF.sub.3 F CH CH CH N i-Pr Me CF.sub.3
F CH CH CH N t-Bu Me CF.sub.3 F CH CH CH N Et Me CF.sub.3 Me CH CH
CH N i-Pr Me CF.sub.3 Me CH CH CH N t-Bu Me CF.sub.3 Me CH CH CH N
Et Me CF.sub.3 CF.sub.3 CH CH CH N i-Pr Me CF.sub.3 CF.sub.3 CH CH
CH N t-Bu Me CF.sub.3 CF.sub.3 CH CH CH N Et Me CF.sub.3 OMe CH CH
CH N i-Pr Me CF.sub.3 OMe CH CH CH N t-Bu Me CF.sub.3 OMe CH CH CH
N Et Me CF.sub.3 CN CH CH CH N i-Pr Me CF.sub.3 CN CH CH CH N t-Bu
Me CF.sub.3 CN CH CH CH N Et Cl CF.sub.3 Cl CH CH CH N i-Pr Cl
CF.sub.3 Cl CH CH CH N t-Bu Cl CF.sub.3 Cl CH CH CH N Et Cl
CF.sub.3 Br CH CH CH N i-Pr Cl CF.sub.3 Br CH CH CH N t-Bu Cl
CF.sub.3 Br CH CH CH N Et Cl CF.sub.3 I CH CH CH N i-Pr Cl CF.sub.3
I CH CH CH N t-Bu Cl CF.sub.3 I CH CH CH N Et Cl CF.sub.3 F CH CH
CH N i-Pr Cl CF.sub.3 F CH CH CH N t-Bu Cl CF.sub.3 F CH CH CH N Et
Cl CF.sub.3 Me CH CH CH N i-Pr Cl CF.sub.3 Me CH CH CH N t-Bu Cl
CF.sub.3 Me CH CH CH N Et Cl CF.sub.3 CF.sub.3 CH CH CH N i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH N t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH N
Et Cl CF.sub.3 OMe CH CH CH N i-Pr Cl CF.sub.3 OMe CH CH CH N t-Bu
Cl CF.sub.3 OMe CH CH CH N Et Cl CF.sub.3 CN CH CH CH N i-Pr Cl
CF.sub.3 CN CH CH CH N t-Bu Cl CF.sub.3 CN CH CH N CH Et Me
CF.sub.3 Cl CH CH N CH i-Pr Me CF.sub.3 Cl CH CH N CH t-Bu Me
CF.sub.3 Cl CH CH N CH Et Me CF.sub.3 Br CH CH N CH i-Pr Me
CF.sub.3 Br CH CH N CH t-Bu Me CF.sub.3 Br CH CH N CH Et Me
CF.sub.3 I CH CH N CH i-Pr Me CF.sub.3 I CH CH N CH t-Bu Me
CF.sub.3 I CH CH N CH Et Me CF.sub.3 F CH CH N CH i-Pr Me CF.sub.3
F CH CH N CH t-Bu Me CF.sub.3 F CH CH N CH Et Me CF.sub.3 Me CH CH
N CH i-Pr Me CF.sub.3 Me CH CH N CH t-Bu Me CF.sub.3 Me CH CH N CH
Et Me CF.sub.3 CF.sub.3 CH CH N CH i-Pr Me CF.sub.3 CF.sub.3 CH CH
N CH t-Bu Me CF.sub.3 CF.sub.3 CH CH N CH Et Me CF.sub.3 OMe CH CH
N CH i-Pr Me CF.sub.3 OMe CH CH N CH t-Bu Me CF.sub.3 OMe CH CH N
CH Et Me CF.sub.3 CN CH CH N CH i-Pr Me CF.sub.3 CN CH CH N CH t-Bu
Me CF.sub.3 CN CH CH N CH Et Cl CF.sub.3 Cl CH CH N CH i-Pr Cl
CF.sub.3 Cl CH CH N CH t-Bu Cl CF.sub.3 Cl CH CH N CH Et Cl
CF.sub.3 Br CH CH N CH i-Pr Cl CF.sub.3 Br CH CH N CH t-Bu Cl
CF.sub.3 Br CH CH N CH Et Cl CF.sub.3 I CH CH N CH i-Pr Cl CF.sub.3
I CH CH N CH t-Bu Cl CF.sub.3 I CH CH N CH Et Cl CF.sub.3 F CH CH N
CH i-Pr Cl CF.sub.3 F CH CH N CH t-Bu Cl CF.sub.3 F CH CH N CH Et
Cl CF.sub.3 Me CH CH N CH i-Pr Cl CF.sub.3 Me CH CH N CH t-Bu Cl
CF.sub.3 Me CH CH N CH Et Cl CF.sub.3 CF.sub.3 CH CH N CH i-Pr Cl
CF.sub.3 CF.sub.3 CH CH N CH t-Bu Cl CF.sub.3 CF.sub.3 CH CH N CH
Et Cl CF.sub.3 OMe CH CH N CH i-Pr Cl CF.sub.3 OMe CH CH N CH t-Bu
Cl CF.sub.3 OMe CH CH N CH Et Cl CF.sub.3 CN CH CH N CH i-Pr Cl
CF.sub.3 CN CH CH N CH t-Bu Cl CF.sub.3 CN CH N CH CH Et Me
CF.sub.3 Cl CH N CH CH i-Pr Me CF.sub.3 Cl CH N CH CH t-Bu Me
CF.sub.3 Cl CH N CH CH Et Me CF.sub.3 Br CH N CH CH i-Pr Me
CF.sub.3 Br CH N CH CH t-Bu Me CF.sub.3 Br CH N CH CH Et Me
CF.sub.3 I CH N CH CH i-Pr Me CF.sub.3 I CH N CH CH t-Bu Me
CF.sub.3 I CH N CH CH Et Me CF.sub.3 F CH N CH CH i-Pr Me CF.sub.3
F CH N CH CH t-Bu Me CF.sub.3 F CH N CH CH Et Me CF.sub.3 Me CH N
CH CH i-Pr Me CF.sub.3 Me CH N CH CH t-Bu Me CF.sub.3 Me CH N CH CH
Et Me CF.sub.3 CF.sub.3 CH N CH CH i-Pr Me CF.sub.3 CF.sub.3 CH N
CH CH t-Bu Me CF.sub.3 CF.sub.3 CH N CH CH Et Me CF.sub.3 OMe CH N
CH CH i-Pr Me CF.sub.3 OMe CH N CH CH t-Bu Me CF.sub.3 OMe CH N CH
CH Et Me CF.sub.3 CN CH N CH CH i-Pr Me CF.sub.3 CN CH N CH CH t-Bu
Me CF.sub.3 CN CH N CH CH Et Cl CF.sub.3 Cl CH N CH CH i-Pr Cl
CF.sub.3 Cl CH N CH CH t-Bu Cl CF.sub.3 Cl CH N CH CH Et Cl
CF.sub.3 Br CH N CH CH i-Pr Cl CF.sub.3 Br CH N CH CH t-Bu Cl
CF.sub.3 Br CH N CH CH Et Cl CF.sub.3 I CH N CH CH i-Pr Cl CF.sub.3
I CH N CH CH t-Bu Cl CF.sub.3 I CH N CH CH Et Cl CF.sub.3 F CH N CH
CH i-Pr Cl CF.sub.3 F CH N CH CH t-Bu Cl CF.sub.3 F CH N CH CH Et
Cl CF.sub.3 Me CH N CH CH i-Pr Cl CF.sub.3 Me CH N CH CH t-Bu Cl
CF.sub.3 Me CH N CH CH Et Cl CF.sub.3 CF.sub.3 CH N CH CH i-Pr Cl
CF.sub.3 CF.sub.3 CH N CH CH t-Bu Cl CF.sub.3 CF.sub.3 CH N CH CH
Et Cl CF.sub.3 OMe CH N CH CH i-Pr Cl CF.sub.3 OMe CH N CH CH t-Bu
Cl CF.sub.3 OMe CH N CH CH Et Cl CF.sub.3 CN CH N CH CH i-Pr Cl
CF.sub.3 CN CH N CH CH t-Bu Cl CF.sub.3 CN N CH CH CH Et Me
CF.sub.3 Cl N CH CH CH i-Pr Me CF.sub.3 Cl N CH CH CH t-Bu Me
CF.sub.3 Cl N CH CH CH Et Me CF.sub.3 Br N CH CH CH i-Pr Me
CF.sub.3 Br N CH CH CH t-Bu Me CF.sub.3 Br N CH CH CH Et Me
CF.sub.3 I N CH CH CH i-Pr Me CF.sub.3 I N CH CH CH t-Bu Me
CF.sub.3 I N CH CH CH Et Me CF.sub.3 F N CH CH CH i-Pr Me CF.sub.3
F N CH CH CH t-Bu Me CF.sub.3 F N CH CH CH Et Me CF.sub.3 Me N CH
CH CH i-Pr Me CF.sub.3 Me N CH CH CH t-Bu Me CF.sub.3 Me N CH CH CH
Et Me CF.sub.3 CF.sub.3 N CH CH CH i-Pr Me CF.sub.3 CF.sub.3 N CH
CH CH t-Bu Me CF.sub.3 CF.sub.3 N CH CH CH Et Me CF.sub.3 OMe N CH
CH CH i-Pr Me CF.sub.3 OMe N CH CH CH t-Bu Me CF.sub.3 OMe N CH CH
CH Et Me CF.sub.3 CN N CH CH CH i-Pr Me CF.sub.3 CN N CH CH CH t-Bu
Me CF.sub.3 CN N CH CH CH Et Cl CF.sub.3 Cl N CH CH CH i-Pr Cl
CF.sub.3 Cl N CH CH CH t-Bu Cl CF.sub.3 Cl N CH CH CH Et Cl
CF.sub.3 Br N CH CH CH i-Pr Cl CF.sub.3 Br N CH CH CH t-Bu Cl
CF.sub.3 Br N CH CH CH Et Cl CF.sub.3 I N CH CH CH i-Pr Cl CF.sub.3
I N CH CH CH t-Bu Cl CF.sub.3 I N CH CH CH Et Cl CF.sub.3 F N CH CH
CH i-Pr Cl CF.sub.3 F N CH CH CH t-Bu Cl CF.sub.3 F N CH CH CH Et
Cl CF.sub.3 Me N CH CH CH i-Pr Cl CF.sub.3 Me N CH CH CH t-Bu Cl
CF.sub.3 Me N CH CH CH Et Cl CF.sub.3 CF.sub.3 N CH CH CH i-Pr Cl
CF.sub.3 CF.sub.3 N CH CH CH t-Bu Cl CF.sub.3 CF.sub.3 N CH CH CH
Et Cl CF.sub.3 OMe N CH CH CH i-Pr Cl CF.sub.3 OMe N CH CH CH t-Bu
Cl CF.sub.3 OMe N CH CH CH Et Cl CF.sub.3 CN N CH CH CH i-Pr Cl
CF.sub.3 CN N CH CH CH t-Bu Cl CF.sub.3 CN CH N CH N Et Me CF.sub.3
Cl CH N CH N i-Pr Me CF.sub.3 Cl CH N CH N t-Bu Me CF.sub.3 Cl CH N
CH N Et Me CF.sub.3 Br CH N CH N i-Pr Me CF.sub.3 Br CH N CH N t-Bu
Me CF.sub.3 Br CH N CH N Et Me CF.sub.3 I CH N CH N i-Pr Me
CF.sub.3 I CH N CH N t-Bu Me CF.sub.3 I CH N CH N Et Me CF.sub.3 F
CH N CH N i-Pr Me CF.sub.3 F CH N CH N t-Bu Me CF.sub.3 F CH N CH N
Et Me CF.sub.3 Me CH N CH N i-Pr Me CF.sub.3 Me CH N CH N t-Bu Me
CF.sub.3 Me CH N CH N Et Me CF.sub.3 CF.sub.3 CH N CH N i-Pr Me
CF.sub.3 CF.sub.3 CH N CH N t-Bu Me CF.sub.3 CF.sub.3 CH N CH N Et
Me CF.sub.3 OMe CH N CH N i-Pr Me CF.sub.3 OMe CH N CH N t-Bu Me
CF.sub.3 OMe CH N CH N Et Me CF.sub.3 CN CH N CH N i-Pr Me CF.sub.3
CN CH N CH N t-Bu Me CF.sub.3 CN CH N CH N Et Cl CF.sub.3 Cl CH N
CH N i-Pr Cl CF.sub.3 Cl CH N CH N t-Bu Cl CF.sub.3 Cl CH N CH N Et
Cl CF.sub.3 Br CH N CH N i-Pr Cl CF.sub.3 Br CH N CH N t-Bu Cl
CF.sub.3 Br CH N CH N Et Cl CF.sub.3 I CH N CH N i-Pr Cl CF.sub.3 I
CH N CH N t-Bu Cl CF.sub.3 I CH N CH N Et Cl CF.sub.3 F CH N CH N
i-Pr Cl CF.sub.3 F CH N CH N t-Bu Cl CF.sub.3 F CH N CH N Et Cl
CF.sub.3 Me CH N CH N i-Pr Cl CF.sub.3 Me CH N CH N t-Bu Cl
CF.sub.3 Me CH N CH N Et Cl CF.sub.3 CF.sub.3 CH N CH N i-Pr Cl
CF.sub.3 CF.sub.3 CH N CH N t-Bu Cl CF.sub.3 CF.sub.3 CH N CH N Et
Cl CF.sub.3 OMe CH N CH N i-Pr Cl CF.sub.3 OMe CH N CH N t-Bu Cl
CF.sub.3 OMe CH N CH N Et Cl CF.sub.3 CN CH N CH N i-Pr Cl CF.sub.3
CN CH N CH N t-Bu Cl CF.sub.3 CN CH CH CH CCl Et Me CF.sub.3 Cl CH
CH CH CCl i-Pr Me CF.sub.3 Cl CH CH CH CCl t-Bu Me CF.sub.3 Cl CH
CH CH CCl Et Me CF.sub.3 Br CH CH CH CCl i-Pr Me CF.sub.3 Br CH CH
CH CCl t-Bu Me CF.sub.3 Br CH CH CH CCl Et Me CF.sub.3 I CH CH CH
CCl i-Pr Me CF.sub.3 I CH CH CH CCl t-Bu Me CF.sub.3 I CH CH CH CCl
Et Me CF.sub.3 F CH CH CH CCl i-Pr Me CF.sub.3 F CH CH CH CCl t-Bu
Me CF.sub.3 F CH CH CH CCl Et Me CF.sub.3 Me CH CH CH CCl i-Pr Me
CF.sub.3 Me CH CH CH CCl t-Bu Me CF.sub.3 Me CH CH CH CCl Et Me
CF.sub.3 CF.sub.3 CH CH CH CCl i-Pr Me CF.sub.3 CF.sub.3 CH CH CH
CCl t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CCl Et Me CF.sub.3 OMe CH CH
CH CCl i-Pr Me CF.sub.3 OMe CH CH CH CCl t-Bu Me CF.sub.3 OMe CH CH
CH CCl Et Me CF.sub.3 CN CH CH CH CCl i-Pr Me CF.sub.3 CN CH CH CH
CCl t-Bu Me CF.sub.3 CN CH CH CH CCl Et Cl CF.sub.3 Cl CH CH CH CCl
i-Pr Cl CF.sub.3 Cl CH CH CH CCl t-Bu Cl CF.sub.3 Cl CH CH CH CCl
Et Cl CF.sub.3 Br CH CH CH CCl i-Pr Cl CF.sub.3 Br CH CH CH CCl
t-Bu Cl CF.sub.3 Br CH CH CH CCl Et Cl CF.sub.3 I CH CH CH CCl i-Pr
Cl CF.sub.3 I CH CH CH CCl t-Bu Cl CF.sub.3 I CH CH CH CCl Et Cl
CF.sub.3 F CH CH CH CCl i-Pr Cl CF.sub.3 F CH CH CH CCl t-Bu Cl
CF.sub.3 F CH CH CH CCl Et Cl CF.sub.3 Me CH CH CH CCl i-Pr Cl
CF.sub.3 Me CH CH CH CCl t-Bu Cl CF.sub.3 Me CH CH CH CCl Et Cl
CF.sub.3 CF.sub.3 CH CH CH CCl i-Pr Cl CF.sub.3 CF.sub.3 CH CH CH
CCl t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CCl Et Cl CF.sub.3 OMe CH CH
CH CCl i-Pr Cl CF.sub.3 OMe CH CH CH CCl t-Bu Cl CF.sub.3 OMe CH CH
CH CCl Et Cl CF.sub.3 CN CH CH CH CCl i-Pr Cl CF.sub.3 CN CH CH CH
CCl t-Bu Cl CF.sub.3 CN CH CH CH CF Et Me CF.sub.3 Cl CH CH CH CF
i-Pr Me CF.sub.3 Cl CH CH CH CF t-Bu Me CF.sub.3 Cl CH CH CH CF Et
Me CF.sub.3 Br CH CH CH CF i-Pr Me CF.sub.3 Br CH CH CH CF t-Bu Me
CF.sub.3 Br CH CH CH CF Et Me CF.sub.3 I CH CH CH CF i-Pr Me
CF.sub.3 I CH CH CH CF t-Bu Me CF.sub.3 I CH CH CH CF Et Me
CF.sub.3 F CH CH CH CF i-Pr Me CF.sub.3 F CH CH CH CF t-Bu Me
CF.sub.3 F CH CH CH CF Et Me CF.sub.3 Me CH CH CH CF i-Pr Me
CF.sub.3 Me CH CH CH CF t-Bu Me CF.sub.3 Me CH CH CH CF Et Me
CF.sub.3 CF.sub.3 CH CH CH CF i-Pr Me CF.sub.3 CF.sub.3 CH CH CH CF
t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CF Et Me CF.sub.3 OMe CH CH CH
CF i-Pr Me CF.sub.3 OMe CH CH CH CF t-Bu Me CF.sub.3 OMe CH CH CH
CF Et Me CF.sub.3 CN CH CH CH CF i-Pr Me CF.sub.3 CN CH CH CH CF
t-Bu Me CF.sub.3 CN CH CH CH CF Et Cl CF.sub.3 Cl CH CH CH CF i-Pr
Cl CF.sub.3 Cl CH CH CH CF t-Bu Cl CF.sub.3 Cl CH CH CH CF Et Cl
CF.sub.3 Br CH CH CH CF i-Pr Cl CF.sub.3 Br CH CH CH CF t-Bu Cl
CF.sub.3 Br CH CH CH CF Et Cl CF.sub.3 I CH CH CH CF i-Pr Cl
CF.sub.3 I CH CH CH CF t-Bu Cl CF.sub.3 I CH CH CH CF i-Pr Cl
CF.sub.3 F CH CH CH CF t-Bu Cl CF.sub.3 F CH CH CH CF Et Cl
CF.sub.3 Me CH CH CH CF i-Pr Cl CF.sub.3 Me CH CH CH CF t-Bu Cl
CF.sub.3 Me CH CH CH CF Et Cl CF.sub.3 CF.sub.3 CH CH CH CF i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH CF t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CF
Et Cl CF.sub.3 OMe CH CH CH CF i-Pr Cl CF.sub.3 OMe CH CH CH CF
t-Bu Cl CF.sub.3 OMe CH CH CH CF Et Cl CF.sub.3 CN CH CH CH CF i-Pr
Cl CF.sub.3 CN CH CH CH CF t-Bu Cl CF.sub.3 CN CH CH CH CH Et Me
C.sub.2F.sub.5 Cl CH CH CH CH i-Pr Me C.sub.2F.sub.5 Cl CH CH CH CH
t-Bu Me C.sub.2F.sub.5 Cl CH CH CH CH Et Me C.sub.2F.sub.5 Br CH CH
CH CH i-Pr Me C.sub.2F.sub.5 Br CH CH CH CH t-Bu Me C.sub.2F.sub.5
Br CH CH CH CH Et Me C.sub.2F.sub.5 I CH CH CH CH i-Pr Me
C.sub.2F.sub.5 I CH CH CH CH t-Bu Me C.sub.2F.sub.5 I CH CH CH CH
Et Me C.sub.2F.sub.5 F CH CH CH CH i-Pr Me C.sub.2F.sub.5 F CH CH
CH CH t-Bu Me C.sub.2F.sub.5 F CH CH CH CH Et Me C.sub.2F.sub.5 Me
CH CH CH CH i-Pr Me C.sub.2F.sub.5 Me CH CH CH CH t-Bu Me
C.sub.2F.sub.5 Me CH CH CH CH Et Me C.sub.2F.sub.5 CF.sub.3 CH CH
CH CH i-Pr Me C.sub.2F.sub.5 CF.sub.3 CH CH CH CH t-Bu Me
C.sub.2F.sub.5 CF.sub.3 CH CH CH CH Et Me C.sub.2F.sub.5 OMe CH CH
CH CH i-Pr Me C.sub.2F.sub.5 OMe CH CH CH CH t-Bu Me C.sub.2F.sub.5
OMe CH CH CH CH Et Me C.sub.2F.sub.5 CN CH CH CH CH i-Pr Me
C.sub.2F.sub.5 CN CH CH CH CH t-Bu Me C.sub.2F.sub.5 CN CH CH CH CH
Et Cl C.sub.2F.sub.5 Cl CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Cl CH CH
CH CH t-Bu Cl C.sub.2F.sub.5 Cl CH CH CH CH Et Cl C.sub.2F.sub.5 Br
CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Br CH CH CH CH t-Bu Cl
C.sub.2F.sub.5 Br CH CH CH CH Et Cl C.sub.2F.sub.5 I CH CH CH CH
i-Pr Cl C.sub.2F.sub.5 I CH CH CH CH t-Bu Cl C.sub.2F.sub.5 I CH CH
CH CH Et Cl C.sub.2F.sub.5 F CH CH CH CH i-Pr Cl C.sub.2F.sub.5 F
CH CH CH CH t-Bu Cl C.sub.2F.sub.5 F CH CH CH CH Et Cl
C.sub.2F.sub.5 Me CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Me CH CH CH CH
t-Bu Cl C.sub.2F.sub.5 Me CH CH CH CH Et Cl C.sub.2F.sub.5 CF.sub.3
CH CH CH CH i-Pr Cl C.sub.2F.sub.5 CF.sub.3 CH CH CH CH t-Bu Cl
C.sub.2F.sub.5 CF.sub.3 CH CH CH CH Et Cl C.sub.2F.sub.5 OMe CH CH
CH CH i-Pr Cl C.sub.2F.sub.5 OMe CH CH CH CH t-Bu Cl C.sub.2F.sub.5
OMe CH CH CH CH Et Cl C.sub.2F.sub.5 CN CH CH CH CH i-Pr Cl
C.sub.2F.sub.5 CN CH CH CH CH t-Bu Cl C.sub.2F.sub.5 CN
[0349]
13TABLE 13 52 W X Y Z R.sup.3 R.sup.4 R.sup.7 R.sup.8 CH CH CH CH
Et Me CF.sub.3 Cl CH CH CH CH i-Pr Me CF.sub.3 Cl CH CH CH CH t-Bu
Me CF.sub.3 Cl CH CH CH CH Et Me CF.sub.3 Br CH CH CH CH i-Pr Me
CF.sub.3 Br CH CH CH CH i-Bu Me CF.sub.3 Br CH CH CH CH Et Me
CF.sub.3 I CH CH CH CH i-Pr Me CF.sub.3 I CH CH CH CH t-Bu Me
CF.sub.3 I CH CH CH CH Et Me CF.sub.3 F CH CH CH CH i-Pr Me
CF.sub.3 F CH CH CH CH t-Bu Me CF.sub.3 F CH CH CH CH Et Me
CF.sub.3 Me CH CH CH CH i-Pr Me CF.sub.3 Me CH CH CH CH t-Bu Me
CF.sub.3 Me CH CH CH CH Et Me CF.sub.3 CF.sub.3 CH CH CH CH i-Pr Me
CF.sub.3 CF.sub.3 CH CH CH CH t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CH
Et Me CF.sub.3 OMe CH CH CH CH i-Pr Me CF.sub.3 OMe CH CH CH CH
t-Bu Me CF.sub.3 OMe CH CH CH CH Et Me CF.sub.3 CN CH CH CH CH i-Pr
Me CF.sub.3 CN CH CH CH CH t-Bu Me CF.sub.3 CN CH CH CH CH Et Cl
CF.sub.3 Cl CH CH CH CH i-Pr Cl CF.sub.3 Cl CH CH CH CH t-Bu Cl
CF.sub.3 Cl CH CH CH CH Et Cl CF.sub.3 Br CH CH CH CH i-Pr Cl
CF.sub.3 Br CH CH CH CH t-Bu Cl CF.sub.3 Br CH CH CH CH Et Cl
CF.sub.3 I CH CH CH CH i-Pr Cl CF.sub.3 I CH CH CH CH t-Bu Cl
CF.sub.3 I CH CH CH CH Et Cl CF.sub.3 F CH CH CH CH i-Pr Cl
CF.sub.3 F CH CH CH CH t-Bu Cl CF.sub.3 F CH CH CH CH Et Cl
CF.sub.3 Me CH CH CH CH i-Pr Cl CF.sub.3 Me CH CH CH CH t-Bu Cl
CF.sub.3 Me CH CH CH CH Et Cl CF.sub.3 CF.sub.3 CH CH CH CH i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH CH t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CH
Et Cl CF.sub.3 OMe CH CH CH CH i-Pr CI CF.sub.3 OMe CH CH CH CH
t-Bu Cl CF.sub.3 OMe CH CH CH CH Et Cl CF.sub.3 CN CH CH CH CH i-Pr
Cl CF.sub.3 CN CH CH CH CH t-Bu Cl CF.sub.3 CN CH CH CH N Et Me
CF.sub.3 Cl CH CH CH N i-Pr Me CF.sub.3 Cl CH CH CH N t-Bu Me
CF.sub.3 Cl CH CH CH N Et Me CF.sub.3 Br CH CH CH N i-Pr Me
CF.sub.3 Br CH CH CH N t-Bu Me CF.sub.3 Br CH CH CH N Et Me
CF.sub.3 I CH CH CH N i-Pr Me CF.sub.3 I CH CH CH N t-Bu Me
CF.sub.3 I CH CH CH N Et Me CF.sub.3 F CH CH CH N i-Pr Me CF.sub.3
F CH CH CH N t-Bu Me CF.sub.3 F CH CH CH N Et Me CF.sub.3 Me CH CH
CH N i-Pr Me CF.sub.3 Me CH CH CH N t-Bu Me CF.sub.3 Me CH CH CH N
Et Me CF.sub.3 CF.sub.3 CH CH CH N i-Pr Me CF.sub.3 CF.sub.3 CH CH
CH N t-Bu Me CF.sub.3 CF.sub.3 CH CH CH N Et Me CF.sub.3 OMe CH CH
CH N i-Pr Me CF.sub.3 OMe CH CH CH N t-Bu Me CF.sub.3 OMe CH CH CH
N Et Me CF.sub.3 CN CH CH CH N i-Pr Me CF.sub.3 CN CH CH CH N t-Bu
Me CF.sub.3 CN CH CH CH N Et Cl CF.sub.3 Cl CH CH CH N i-Pr Cl
CF.sub.3 Cl CH CH CH N t-Bu Cl CF.sub.3 Cl CH CH CH N Et Cl
CF.sub.3 Br CH CH CH N i-Pr Cl CF.sub.3 Br CH CH CH N t-Bu Cl
CF.sub.3 Br CH CH CH N Et Cl CF.sub.3 I CH CH CH N i-Pr Cl CF.sub.3
I CH CH CH N t-Bu Cl CF.sub.3 I CH CH CH N Et Cl CF.sub.3 F CH CH
CH N i-Pr Cl CF.sub.3 F CH CH CH N t-Bu Cl CF.sub.3 F CH CH CH N Et
Cl CF.sub.3 Me CH CH CH N i-Pr Cl CF.sub.3 Me CH CH CH N t-Bu Cl
CF.sub.3 Me CH CH CH N Et Cl CF.sub.3 CF.sub.3 CH CH CH N i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH N t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH N
Et Cl CF.sub.3 OMe CH CH CH N i-Pr Cl CF.sub.3 OMe CH CH CH N t-Bu
Cl CF.sub.3 OMe CH CH CH N Et Cl CF.sub.3 CN CH CH CH N i-Pr Cl
CF.sub.3 CN CH CH CH N t-Bu Cl CF.sub.3 CN CH CH N CH Et Me
CF.sub.3 Cl CH CH N CH i-Pr Me CF.sub.3 Cl CH CH N CH t-Bu Me
CF.sub.3 Cl CH CH N CH Et Me CF.sub.3 Br CH CH N CH i-Pr Me
CF.sub.3 Br CH CH N CH t-Bu Me CF.sub.3 Br CH CH N CH Et Me
CF.sub.3 I CH CH N CH i-Pr Me CF.sub.3 I CH CH N CH t-Bu Me
CF.sub.3 I CH CH N CH Et Me CF.sub.3 F CH CH N CH i-Pr Me CF.sub.3
F CH CH N CH t-Bu Me CF.sub.3 F CH CH N CH Et Me CF.sub.3 Me CH CH
N CH i-Pr Me CF.sub.3 Me CH CH N CH t-Bu Me CF.sub.3 Me CH CH N CH
Et Me CF.sub.3 CF.sub.3 CH CH N CH i-Pr Me CF.sub.3 CF.sub.3 CH CH
N CH t-Bu Me CF.sub.3 CF.sub.3 CH CH N CH Et Me CF.sub.3 OMe CH CH
N CH i-Pr Me CF.sub.3 OMe CH CH N CH t-Bu Me CF.sub.3 OMe CH CH N
CH Et Me CF.sub.3 CN CH CH N CH i-Pr Me CF.sub.3 CN CH CH N CH t-Bu
Me CF.sub.3 CN CH CH N CH Et Cl CF.sub.3 Cl CH CH N CH i-Pr Cl
CF.sub.3 Cl CH CH N CH t-Bu Cl CF.sub.3 Cl CH CH N CH Et Cl
CF.sub.3 Br CH CH N CH i-Pr Cl CF.sub.3 Br CH CH N CH t-Bu Cl
CF.sub.3 Br CH CH N CH Et Cl CF.sub.3 I CH CH N CH i-Pr Cl CF.sub.3
I CH CH N CH t-Bu Cl CF.sub.3 I CH CH N CH Et Cl CF.sub.3 F CH CH N
CH i-Pr Cl CF.sub.3 F CH CH N CH t-Bu Cl CF.sub.3 F CH CH N CH Et
Cl CF.sub.3 Me CH CH N CH i-Pr Cl CF.sub.3 Me CH CH N CH t-Bu Cl
CF.sub.3 Me CH CH N CH Et Cl CF.sub.3 CF.sub.3 CH CH N CH i-Pr Cl
CF.sub.3 CF.sub.3 CH CH N CH t-Bu Cl CF.sub.3 CF.sub.3 CH CH N CH
Et Cl CF.sub.3 OMe CH CH N CH i-Pr Cl CF.sub.3 OMe CH CH N CH t-Bu
Cl CF.sub.3 OMe CH CH N CH Et Cl CF.sub.3 CN CH CH N CH i-Pr Cl
CF.sub.3 CN CH CH N CH t-Bu Cl CF.sub.3 CN CH N CH CH Et Me
CF.sub.3 Cl CH N CH CH i-Pr Me CF.sub.3 Cl CH N CH CH t-Bu Me
CF.sub.3 Cl CH N CH CH Et Me CF.sub.3 Br CH N CH CH i-Pr Me
CF.sub.3 Br CH N CH CH t-Bu Me CF.sub.3 Br CH N CH CH Et Me
CF.sub.3 I CH N CH CH i-Pr Me CF.sub.3 I CH N CH CH t-Bu Me
CF.sub.3 I CH N CH CH Et Me CF.sub.3 F CH N CH CH i-Pr Me CF.sub.3
F CH N CH CH t-Bu Me CF.sub.3 F CH N CH CH Et Me CF.sub.3 Me CH N
CH CH i-Pr Me CF.sub.3 Me CH N CH CH t-Bu Me CF.sub.3 Me CH N CH CH
Et Me CF.sub.3 CF.sub.3 CH N CH CH i-Pr Me CF.sub.3 CF.sub.3 CH N
CH CH t-Bu Me CF.sub.3 CF.sub.3 CH N CH CH Et Me CF.sub.3 OMe CH N
CH CH i-Pr Me CF.sub.3 OMe CH N CH CH t-Bu Me CF.sub.3 OMe CH N CH
CH Et Me CF.sub.3 CN CH N CH CH i-Pr Me CF.sub.3 CN CH N CH CH t-Bu
Me CF.sub.3 CN CH N CH CH Et Cl CF.sub.3 Cl CH N CH CH i-Pr Cl
CF.sub.3 Cl CH N CH CH t-Bu Cl CF.sub.3 Cl CH N CH CH Et Cl
CF.sub.3 Br CH N CH CH i-Pr Cl CF.sub.3 Br CH N CH CH t-Bu Cl
CF.sub.3 Br CH N CH CH Et Cl CF.sub.3 I CH N CH CH i-Pr Cl CF.sub.3
I CH N CH CH t-Bu Cl CF.sub.3 I CH N CH CH Et Cl CF.sub.3 F CH N CH
CH i-Pr Cl CF.sub.3 F CH N CH CH t-Bu Cl CF.sub.3 F CH N CH CH Et
Cl CF.sub.3 Me CH N CH CH i-Pr Cl CF.sub.3 Me CH N CH CH t-Bu Cl
CF.sub.3 Me CH N CH CH Et Cl CF.sub.3 CF.sub.3 CH N CH CH i-Pr Cl
CF.sub.3 CF.sub.3 CH N CH CH t-Bu Cl CF.sub.3 CF.sub.3 CH N CH CH
Et Cl CF.sub.3 OMe CH N CH CH i-Pr Cl CF.sub.3 OMe CH N CH CH t-Bu
Cl CF.sub.3 OMe CH N CH CH Et Cl CF.sub.3 CN CH N CH CH i-Pr Cl
CF.sub.3 CN CH N CH CH t-Bu Cl CF.sub.3 CN N CH CH CH Et Me
CF.sub.3 Cl N CH CH CH i-Pr Me CF.sub.3 Cl N CH CH CH t-Bu Me
CF.sub.3 Cl N CH CH CH Et Me CF.sub.3 Br N CH CH CH i-Pr Me
CF.sub.3 Br N CH CH CH t-Bu Me CF.sub.3 Br N CH CH CH Et Me
CF.sub.3 I N CH CH CH i-Pr Me CF.sub.3 I N CH CH CH t-Bu Me
CF.sub.3 I N CH CH CH Et Me CF.sub.3 F N CH CH CH i-Pr Me CF.sub.3
F N CH CH CH t-Bu Me CF.sub.3 F N CH CH CH Et Me CF.sub.3 Me N CH
CH CH i-Pr Me CF.sub.3 Me N CH CH CH t-Bu Me CF.sub.3 Me N CH CH CH
Et Me CF.sub.3 CF.sub.3 N CH CH CH i-Pr Me CF.sub.3 CF.sub.3 N CH
CH CH t-Bu Me CF.sub.3 CF.sub.3 N CH CH CH Et Me CF.sub.3 OMe N CH
CH CH i-Pr Me CF.sub.3 OMe N CH CH CH t-Bu Me CF.sub.3 OMe N CH CH
CH Et Me CF.sub.3 CN N CH CH CH i-Pr Me CF.sub.3 CN N CH CH CH t-Bu
Me CF.sub.3 CN N CH CH CH Et Cl CF.sub.3 Cl N CH CH CH i-Pr Cl
CF.sub.3 Cl N CH CH CH t-Bu Cl CF.sub.3 Cl N CH CH CH Et Cl
CF.sub.3 Br N CH CH CH i-Pr Cl CF.sub.3 Br N CH CH CH t-Bu Cl
CF.sub.3 Br N CH CH CH Et Cl CF.sub.3 I N CH CH CH i-Pr Cl CF.sub.3
I N CH CH CH t-Bu Cl CF.sub.3 I N CH CH CH Et Cl CF.sub.3 F N CH CH
CH i-Pr Cl CF.sub.3 F N CH CH CH t-Bu Cl CF.sub.3 F N CH CH CH Et
Cl CF.sub.3 Me N CH CH CH i-Pr Cl CF.sub.3 Me N CH CH CH t-Bu Cl
CF.sub.3 Me N CH CH CH Et Cl CF.sub.3 CF.sub.3 N CH CH CH i-Pr Cl
CF.sub.3 CF.sub.3 N CH CH CH t-Bu Cl CF.sub.3 CF.sub.3 N CH CH CH
Et Cl CF.sub.3 OMe N CH CH CH i-Pr Cl CF.sub.3 OMe N CH CH CH t-Bu
Cl CF.sub.3 OMe N CH CH CH Et Cl CF.sub.3 CN N CH CH CH i-Pr Cl
CF.sub.3 CN N CH CH CH t-Bu Cl CF.sub.3 CN CH N CH N Et Me CF.sub.3
Cl CH N CH N i-Pr Me CF.sub.3 Cl CH N CH N t-Bu Me CF.sub.3 Cl CH N
CH N Et Me CF.sub.3 Br CH N CH N i-Pr Me CF.sub.3 Br CH N CH N t-Bu
Me CF.sub.3 Br CH N CH N Et Me CF.sub.3 I CH N CH N i-Pr Me
CF.sub.3 I CH N CH N t-Bu Me CF.sub.3 I CH N CH N Et Me CF.sub.3 F
CH N CH N i-Pr Me CF.sub.3 F CH N CH N t-Bu Me CF.sub.3 F CH N CH N
Et Me CF.sub.3 Me CH N CH N i-Pr Me CF.sub.3 Me CH N CH N t-Bu Me
CF.sub.3 Me CH N CH N Et Me CF.sub.3 CF.sub.3 CH N CH N i-Pr Me
CF.sub.3 CF.sub.3 CH N CH N t-Bu Me CF.sub.3 CF.sub.3 CH N CH N Et
Me CF.sub.3 OMe CH N CH N i-Pr Me CF.sub.3 OMe CH N CH N t-Bu Me
CF.sub.3 OMe CH N CH N Et Me CF.sub.3 CN CH N CH N i-Pr Me CF.sub.3
CN CH N CH N t-Bu Me CF.sub.3 CN CH N CH N Et Cl CF.sub.3 Cl CH N
CH N i-Pr Cl CF.sub.3 Cl CH N CH N t-Bu Cl CF.sub.3 Cl CH N CH N Et
Cl CF.sub.3 Br CH N CH N i-Pr Cl CF.sub.3 Br CH N CH N t-Bu Cl
CF.sub.3 Br CH N CH N Et Cl CF.sub.3 I CH N CH N i-Pr Cl CF.sub.3 I
CH N CH N t-Bu Cl CF.sub.3 I CH N CH N Et Cl CF.sub.3 F CH N CH N
i-Pr Cl CF.sub.3 F CH N CH N t-Bu Cl CF.sub.3 F CH N CH N Et Cl
CF.sub.3 Me CH N CH N i-Pr Cl CF.sub.3 Me CH N CH N t-Bu Cl
CF.sub.3 Me CH N CH N Et Cl CF.sub.3 CF.sub.3 CH N CH N i-Pr Cl
CF.sub.3 CF.sub.3 CH N CH N t-Bu Cl CF.sub.3 CF.sub.3 CH N CH N Et
Cl CF.sub.3 OMe CH N CH N i-Pr Cl CF.sub.3 OMe CH N CH N t-Bu Cl
CF.sub.3 OMe CH N CH N Et Cl CF.sub.3 CN CH N CH N i-Pr Cl CF.sub.3
CN CH N CH N t-Bu Cl CF.sub.3 CN CH CH CH CCl Et Me CF.sub.3 Cl CH
CH CH CCl i-Pr Me CF.sub.3 Cl CH CH CH CCl t-Bu Me CF.sub.3 Cl CH
CH CH CCl Et Me CF.sub.3 Br CH CH CH CCl i-Pr Me CF.sub.3 Br CH CH
CH CCl t-Bu Me CF.sub.3 Br CH CH CH CCl Et Me CF.sub.3 I CH CH CH
CCl i-Pr Me CF.sub.3 I CH CH CH CCl t-Bu Me CF.sub.3 I CH CH CH CCl
Et Me CF.sub.3 F CH CH CH CCl i-Pr Me CF.sub.3 F CH CH CH CCl t-Bu
Me CF.sub.3 F CH CH CH CCl Et Me CF.sub.3 Me CH CH CH CCl i-Pr Me
CF.sub.3 Me CH CH CH CCl t-Bu Me CF.sub.3 Me CH CH CH CCl Et Me
CF.sub.3 CF.sub.3 CH CH CH CCl i-Pr Me CF.sub.3 CF.sub.3 CH CH CH
CCl t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CCl Et Me CF.sub.3 OMe CH CH
CH CCl i-Pr Me CF.sub.3 OMe CH CH CH CCl t-Bu Me CF.sub.3 OMe CH CH
CH CCl Et Me CF.sub.3 CN CH CH CH CCl i-Pr Me CF.sub.3 CN CH CH CH
CCl t-Bu Me CF.sub.3 CN CH CH CH CCl Et Cl CF.sub.3 Cl CH CH CH CCl
i-Pr Cl CF.sub.3 Cl CH CH CH CCl t-Bu Cl CF.sub.3 Cl CH CH CH CCl
Et Cl CF.sub.3 Br CH CH CH CCl i-Pr Cl CF.sub.3 Br CH CH CH CCl
i-Bu Cl CF.sub.3 Br CH CH CH CCl Et Cl CF.sub.3 I CH CH CH CCl i-Pr
Cl CF.sub.3 I CH CH CH CCl t-Bu Cl CF.sub.3 I CH CH CH CCl Et Cl
CF.sub.3 F CH CH CH CCl i-Pr Cl CF.sub.3 F CH CH CH CCl t-Bu Cl
CF.sub.3 F CH CH CH CCl Et Cl CF.sub.3 Me CH CH CH CCl i-Pr Cl
CF.sub.3 Me CH CH CH CCl t-Bu Cl CF.sub.3 Me CH CH CH CCl Et Cl
CF.sub.3 CF.sub.3 CH CH CH CCl i-Pr Cl CF.sub.3 CF.sub.3 CH CH CH
CCl t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CCl Et Cl CF.sub.3 OMe CH CH
CH CCl i-Pr Cl CF.sub.3 OMe CH CH CH CCl t-Bu Cl CF.sub.3 OMe CH CH
CH CCl Et Cl CF.sub.3 CN CH CH CH CCl i-Pr Cl CF.sub.3 CN CH CH CH
CCl t-Bu Cl CF.sub.3 CN CH CH CH CF Et Me CF.sub.3 Cl CH CH CH CF
i-Pr Me CF.sub.3 Cl CH CH CH CF t-Bu Me CF.sub.3 Cl CH CH CH CF Et
Me CF.sub.3 Br CH CH CH CF i-Pr Me CF.sub.3 Br CH CH CH CF t-Bu Me
CF.sub.3 Br CH CH CH CF Et Me CF.sub.3 I CH CH CH CF i-Pr Me
CF.sub.3 I CH CH CH CF t-Bu Me CF.sub.3 I CH CH CH CF Et Me
CF.sub.3 F CH CH CH CF i-Pr Me CF.sub.3 F CH CH CH CF t-Bu Me
CF.sub.3 F CH CH CH CF Et Me CF.sub.3 Me CH CH CH CF i-Pr Me
CF.sub.3 Me CH CH CH CF t-Bu Me CF.sub.3 Me CH CH CH CF Et Me
CF.sub.3 CF.sub.3 CH CH CH CF i-Pr Me CF.sub.3 CF.sub.3 CH CH CH CF
t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CF Et Me CF.sub.3 OMe CH CH CH
CF i-Pr Me CF.sub.3 OMe CH CH CH CF t-Bu Me CF.sub.3 OMe CH CH CH
CF Et Me CF.sub.3 CN CH CH CH CF i-Pr Me CF.sub.3 CN CH CH CH CF
t-Bu Me CF.sub.3 CN CH CH CH CF Et Cl CF.sub.3 Cl CH CH CH CF i-Pr
Cl CF.sub.3 Cl CH CH CH CF t-Bu Cl CF.sub.3 Cl CH CH CH CF Et Cl
CF.sub.3 Br CH CH CH CF i-Pr Cl CF.sub.3 Br CH CH CH CF t-Bu Cl
CF.sub.3 Br CH CH CH CF Et Cl CF.sub.3 I CH CH CH CF i-Pr Cl
CF.sub.3 I CH CH CH CF t-Bu Cl CF.sub.3 I CH CH CH CF i-Pr Cl
CF.sub.3 F CH CH CH CF t-Bu Cl CF.sub.3 F CH CH CH CF Et Cl
CF.sub.3 Me CH CH CH CF i-Pr Cl CF.sub.3 Me CH CH CH CF t-Bu Cl
CF.sub.3 Me CH CH CH CF Et Cl CF.sub.3 CF.sub.3 CH CH CH CF i-Pr CI
CF.sub.3 CF.sub.3 CH CH CH CF t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CF
Et Cl CF.sub.3 OMe CH CH CH CF i-Pr Cl CF.sub.3 OMe CH CH CH CF
t-Bu Cl CF.sub.3 OMe CH CH CH CF Et Cl CF.sub.3 CN CH CH CH CF i-Pr
Cl CF.sub.3 CN CH CH CH CF t-Bu Cl CF.sub.3 CN CH CH CH CH Et Me
C.sub.2F.sub.5 Cl CH CH CH CH i-Pr Me C.sub.2F.sub.5 Cl CH CH CH CH
t-Bu Me C.sub.2F.sub.5 Cl CH CH CH CH Et Me C.sub.2F.sub.5 Br CH CH
CH CH i-Pr Me C.sub.2F.sub.5 Br CH CH CH CH t-Bu Me C.sub.2F.sub.5
Br CH CH CH CH Et Me C.sub.2F.sub.5 I CH CH CH CH i-Pr Me
C.sub.2F.sub.5 I CH CH CH CH t-Bu Me C.sub.2F.sub.5 I CH CH CH CH
Et Me C.sub.2F.sub.5 F CH CH CH CH i-Pr Me C.sub.2F.sub.5 F CH CH
CH CH t-Bu Me C.sub.2F.sub.5 F CH CH CH CH Et Me C.sub.2F.sub.5 Me
CH CH CH CH i-Pr Me C.sub.2F.sub.5 Me CH CH CH CH t-Bu Me
C.sub.2F.sub.5 Me CH CH CH CH Et Me C.sub.2F.sub.5 CF.sub.3 CH CH
CH CH i-Pr Me C.sub.2F.sub.5 CF.sub.3 CH CH CH CH t-Bu Me
C.sub.2F.sub.5 CF.sub.3 CH CH CH CH Et Me C.sub.2F.sub.5 OMe CH CH
CH CH i-Pr Me C.sub.2F.sub.5 OMe CH CH CH CH t-Bu Me C.sub.2F.sub.5
OMe CH CH CH CH Et Me C.sub.2F.sub.5 CN CH CH CH CH i-Pr Me
C.sub.2F.sub.5 CN CH CH CH CH t-Bu Me C.sub.2F.sub.5 CN CH CH CH CH
Et Cl C.sub.2F.sub.5 Cl CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Cl CH CH
CH CH t-Bu Cl C.sub.2F.sub.5 Cl CH CH CH CH Et Cl C.sub.2F.sub.5 Br
CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Br CH CH CH CH t-Bu Cl
C.sub.2F.sub.5 Br CH CH CH CH Et Cl C.sub.2F.sub.5 I CH CH CH CH
i-Pr Cl C.sub.2F.sub.5 I CH CH CH CH t-Bu Cl C.sub.2F.sub.5 I CH CH
CH CH Et Cl C.sub.2F.sub.5 F CH CH CH CH i-Pr Cl C.sub.2F.sub.5 F
CH CH CH CH t-Bu Cl C.sub.2F.sub.5 F CH CH CH CH Et Cl
C.sub.2F.sub.5 Me CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Me CH CH CH CH
t-Bu Cl C.sub.2F.sub.5 Me CH CH CH CH Et Cl C.sub.2F.sub.5 CF.sub.3
CH CH CH CH i-Pr Cl C.sub.2F.sub.5 CF.sub.3 CH CH CH CH t-Bu Cl
C.sub.2F.sub.5 CF.sub.3 CH CH CH CH Et Cl C.sub.2F.sub.5 OMe CH CH
CH CH i-Pr Cl C.sub.2F.sub.5 OMe CH CH CH CH t-Bu Cl C.sub.2F.sub.5
OMe CH CH CH CH Et Cl C.sub.2F.sub.5 CN CH CH CH CH i-Pr Cl
C.sub.2F.sub.5 CN CH CH CH CH t-Bu Cl C.sub.2F.sub.5 CN
[0350]
14TABLE 14 53 W X Y Z R.sup.3 R.sup.4 R.sup.7 R.sup.8 CH CH CH CH
Et Me CF.sub.3 Cl CH CH CH CH i-Pr Me CF.sub.3 Cl CH CH CH CH t-Bu
Me CF.sub.3 Cl CH CH CH CH Et Me CF.sub.3 Br CH CH CH CH i-Pr Me
CF.sub.3 Br CH CH CH CH t-Bu Me CF.sub.3 Br CH CH CH CH Et Me
CF.sub.3 I CH CH CH CH i-Pr Me CF.sub.3 I CH CH CH CH t-Bu Me
CF.sub.3 I CH CH CH CH Et Me CF.sub.3 F CH CH CH CH i-Pr Me
CF.sub.3 F CH CH CH CH t-Bu Me CF.sub.3 F CH CH CH CH Et Me
CF.sub.3 Me CH CH CH CH i-Pr Me CF.sub.3 Me CH CH CH CH t-Bu Me
CF.sub.3 Me CH CH CH CH Et Me CF.sub.3 CF.sub.3 CH CH CH CH i-Pr Me
CF.sub.3 CF.sub.3 CH CH CH CH t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CH
Et Me CF.sub.3 OMe CH CH CH CH i-Pr Me CF.sub.3 OMe CH CH CH CH
t-Bu Me CF.sub.3 OMe CH CH CH CH Et Me CF.sub.3 CN CH CH CH CH i-Pr
Me CF.sub.3 CN CH CH CH CH t-Bu Me CF.sub.3 CN CH CH CH CH Et Cl
CF.sub.3 Cl CH CH CH CH i-Pr Cl CF.sub.3 Cl CH CH CH CH t-Bu Cl
CF.sub.3 Cl CH CH CH CH Et Cl CF.sub.3 Br CH CH CH CH i-Pr Cl
CF.sub.3 Br CH CH CH CH t-Bu Cl CF.sub.3 Br CH CH CH CH Et Cl
CF.sub.3 I CH CH CH CH i-Pr Cl CF.sub.3 I CH CH CH CH t-Bu Cl
CF.sub.3 I CH CH CH CH Et Cl CF.sub.3 F CH CH CH CH i-Pr Cl
CF.sub.3 F CH CH CH CH t-Bu Cl CF.sub.3 F CH CH CH CH Et Cl
CF.sub.3 Me CH CH CH CH i-Pr Cl CF.sub.3 Me CH CH CH CH t-Bu Cl
CF.sub.3 Me CH CH CH CH Et Cl CF.sub.3 CF.sub.3 CH CH CH CH i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH CH t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CH
Et Cl CF.sub.3 OMe CH CH CH CH i-Pr Cl CF.sub.3 OMe CH CH CH CH
t-Bu Cl CF.sub.3 OMe CH CH CH CH Et Cl CF.sub.3 CN CH CH CH CH i-Pr
Cl CF.sub.3 CN CH CH CH CH t-Bu Cl CF.sub.3 CN CH CH CH N Et Me
CF.sub.3 Cl CH CH CH N i-Pr Me CF.sub.3 Cl CH CH CH N t-Bu Me
CF.sub.3 Cl CH CH CH N Et Me CF.sub.3 Br CH CH CH N i-Pr Me
CF.sub.3 Br CH CH CH N t-Bu Me CF.sub.3 Br CH CH CH N Et Me
CF.sub.3 I CH CH CH N i-Pr Me CF.sub.3 I CH CH CH N t-Bu Me
CF.sub.3 I CH CH CH N Et Me CF.sub.3 F CH CH CH N i-Pr Me CF.sub.3
F CH CH CH N t-Bu Me CF.sub.3 F CH CH CH N Et Me CF.sub.3 Me CH CH
CH N i-Pr Me CF.sub.3 Me CH CH CH N t-Bu Me CF.sub.3 Me CH CH CH N
Et Me CF.sub.3 CF.sub.3 CH CH CH N i-Pr Me CF.sub.3 CF.sub.3 CH CH
CH N t-Bu Me CF.sub.3 CF.sub.3 CH CH CH N Et Me CF.sub.3 OMe CH CH
CH N i-Pr Me CF.sub.3 OMe CH CH CH N t-Bu Me CF.sub.3 OMe CH CH CH
N Et Me CF.sub.3 CN CH CH CH N i-Pr Me CF.sub.3 CN CH CH CH N t-Bu
Me CF.sub.3 CN CH CH CH N Et Cl CF.sub.3 Cl CH CH CH N i-Pr Cl
CF.sub.3 Cl CH CH CH N t-Bu Cl CF.sub.3 Cl CH CH CH N Et Cl
CF.sub.3 Br CH CH CH N i-Pr Cl CF.sub.3 Br CH CH CH N t-Bu Cl
CF.sub.3 Br CH CH CH N Et Cl CF.sub.3 I CH CH CH N i-Pr Cl CF.sub.3
I CH CH CH N t-Bu Cl CF.sub.3 I CH CH CH N Et Cl CF.sub.3 F CH CH
CH N i-Pr Cl CF.sub.3 F CH CH CH N t-Bu Cl CF.sub.3 F CH CH CH N Et
Cl CF.sub.3 Me CH CH CH N i-Pr Cl CF.sub.3 Me CH CH CH N t-Bu Cl
CF.sub.3 Me CH CH CH N Et Cl CF.sub.3 CF.sub.3 CH CH CH N i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH N t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH N
Et Cl CF.sub.3 OMe CH CH CH N i-Pr Cl CF.sub.3 OMe CH CH CH N t-Bu
Cl CF.sub.3 OMe CH CH CH N Et Cl CF.sub.3 CN CH CH CH N i-Pr Cl
CF.sub.3 CN CH CH CH N t-Bu Cl CF.sub.3 CN CH CH N CH Et Me
CF.sub.3 Cl CH CH N CH i-Pr Me CF.sub.3 Cl CH CH N CH t-Bu Me
CF.sub.3 Cl CH CH N CH Et Me CF.sub.3 Br CH CH N CH i-Pr Me
CF.sub.3 Br CH CH N CH t-Bu Me CF.sub.3 Br CH CH N CH Et Me
CF.sub.3 I CH CH N CH i-Pr Me CF.sub.3 I CH CH N CH t-Bu Me
CF.sub.3 I CH CH N CH Et Me CF.sub.3 F CH CH N CH i-Pr Me CF.sub.3
F CH CH N CH t-Bu Me CF.sub.3 F CH CH N CH Et Me CF.sub.3 Me CH CH
N CH i-Pr Me CF.sub.3 Me CH CH N CH t-Bu Me CF.sub.3 Me CH CH N CH
Et Me CF.sub.3 CF.sub.3 CH CH N CH i-Pr Me CF.sub.3 CF.sub.3 CH CH
N CH t-Bu Me CF.sub.3 CF.sub.3 CH CH N CH Et Me CF.sub.3 OMe CH CH
N CH i-Pr Me CF.sub.3 OMe CH CH N CH t-Bu Me CF.sub.3 OMe CH CH N
CH Et Me CF.sub.3 CN CH CH N CH i-Pr Me CF.sub.3 CN CH CH N CH t-Bu
Me CF.sub.3 CN CH CH N CH Et Cl CF.sub.3 Cl CH CH N CH i-Pr Cl
CF.sub.3 Cl CH CH N CH t-Bu Cl CF.sub.3 Cl CH CH N CH Et Cl
CF.sub.3 Br CH CH N CH i-Pr Cl CF.sub.3 Br CH CH N CH t-Bu Cl
CF.sub.3 Br CH CH N CH Et Cl CF.sub.3 I CH CH N CH i-Pr Cl CF.sub.3
I CH CH N CH t-Bu Cl CF.sub.3 I CH CH N CH Et Cl CF.sub.3 F CH CH N
CH i-Pr Cl CF.sub.3 F CH CH N CH t-Bu Cl CF.sub.3 F CH CH N CH Et
Cl CF.sub.3 Me OH CH N CH i-Pr Cl CF.sub.3 Me CH CH N CH t-Bu Cl
CF.sub.3 Me CH CH N CH Et Cl CF.sub.3 CF.sub.3 CH CH N CH i-Pr Cl
CF.sub.3 CF.sub.3 CH CH N CH t-Bu Cl CF.sub.3 CF.sub.3 CH CH N CH
Et Cl CF.sub.3 OMe CH CH N CH i-Pr Cl CF.sub.3 OMe CH CH N CH t-Bu
Cl CF.sub.3 OMe CH CH N CH Et Cl CF.sub.3 CN CH CH N CH i-Pr Cl
CF.sub.3 CN CH CH N CH t-Bu Cl CF.sub.3 CN CH N CH CH Et Me
CF.sub.3 Cl CH N CH CH i-Pr Me CF.sub.3 Cl CH N CH CH t-Bu Me
CF.sub.3 Cl CH N CH CH Et Me CF.sub.3 Br CH N CH CH i-Pr Me
CF.sub.3 Br CH N CH CH t-Bu Me CF.sub.3 Br CH N CH CH Et Me
CF.sub.3 I CH N CH CH i-Pr Me CF.sub.3 I CH N CH CH t-Bu Me
CF.sub.3 I CH N CH CH Et Me CF.sub.3 F CH N CH CH i-Pr Me CF.sub.3
F CH N CH CH t-Bu Me CF.sub.3 F CH N CH CH Et Me CF.sub.3 Me CH N
CH CH i-Pr Me CF.sub.3 Me CH N CH CH t-Bu Me CF.sub.3 Me CH N CH CH
Et Me CF.sub.3 CF.sub.3 CH N CH CH i-Pr Me CF.sub.3 CF.sub.3 CH N
CH CH t-Bu Me CF.sub.3 CF.sub.3 CH N CH CH Et Me CF.sub.3 OMe CH N
CH CH i-Pr Me CF.sub.3 OMe CH N CH CH t-Bu Me CF.sub.3 OMe CH N CH
CH Et Me CF.sub.3 CN CH N CH CH i-Pr Me CF.sub.3 CN CH N CH CH t-Bu
Me CF.sub.3 CN CH N CH CH Et Cl CF.sub.3 Cl CH N CH CH i-Pr Cl
CF.sub.3 Cl CH N CH CH t-Bu Cl CF.sub.3 Cl CH N CH CH Et Cl
CF.sub.3 Br CH N CH CH i-Pr Cl CF.sub.3 Br CH N CH CH t-Bu Cl
CF.sub.3 Br CH N CH CH Et Cl CF.sub.3 I CH N CH CH i-Pr Cl CF.sub.3
I CH N CH CH t-Bu Cl CF.sub.3 I CH N CH CH Et Cl CF.sub.3 F CH N CH
CH i-Pr Cl CF.sub.3 F CH N CH CH t-Bu Cl CF.sub.3 F CH N CH CH Et
Cl CF.sub.3 Me CH N CH CH i-Pr Cl CF.sub.3 Me CH N CH CH t-Bu Cl
CF.sub.3 Me CH N CH CH Et Cl CF.sub.3 CF.sub.3 CH N CH CH i-Pr Cl
CF.sub.3 CF.sub.3 CH N CH CH t-Bu Cl CF.sub.3 CF.sub.3 CH N CH CH
Et Cl CF.sub.3 OMe CH N CH CH i-Pr Cl CF.sub.3 OMe CH N CH CH t-Bu
Cl CF.sub.3 OMe CH N CH CH Et Cl CF.sub.3 CN CH N CH CH i-Pr Cl
CF.sub.3 CN CH N CH CH t-Bu Cl CF.sub.3 CN N CH CH CH Et Me
CF.sub.3 Cl N CH CH CH i-Pr Me CF.sub.3 Cl N CH CH CH t-Bu Me
CF.sub.3 Cl N CH CH CH Et Me CF.sub.3 Br N CH CH CH i-Pr Me
CF.sub.3 Br N CH CH CH t-Bu Me CF.sub.3 Br N CH CH CH Et Me
CF.sub.3 I N CH CH CH i-Pr Me CF.sub.3 I N CH CH CH t-Bu Me
CF.sub.3 I N CH CH CH Et Me CF.sub.3 F N CH CH C H i-Pr Me CF.sub.3
F N CH CH CH t-Bu Me CF.sub.3 F N CH CH CH Et Me CF.sub.3 Me N CH
CH CH i-Pr Me CF.sub.3 Me N CH CH CH t-Bu Me CF.sub.3 Me N CH CH CH
Et Me CF.sub.3 CF.sub.3 N CH CH CH i-Pr Me CF.sub.3 CF.sub.3 N CH
CH CH t-Bu Me CF.sub.3 CF.sub.3 N CH CH CH Et Me CF.sub.3 OMe N CH
CH CH i-Pr Me CF.sub.3 OMe N CH CH CH t-Bu Me CF.sub.3 OMe N CH CH
CH Et Me CF.sub.3 CN N CH CH CH i-Pr Me CF.sub.3 CN N CH CH CH t-Bu
Me CF.sub.3 CN N CH CH CH Et Cl CF.sub.3 Cl N CH CH CH i-Pr Cl
CF.sub.3 Cl N CH CH CH t-Bu Cl CF.sub.3 Cl N CH CH CH Et Cl
CF.sub.3 Br N CH CH CH i-Pr Cl CF.sub.3 Br N CH CH CH t-Bu Cl
CF.sub.3 Br N CH CH CH Et Cl CF.sub.3 I N CH CH CH i-Pr Cl CF.sub.3
I N CH CH CH t-Bu Cl CF.sub.3 I N CH CH CH Et Cl CF.sub.3 F N CH CH
CH i-Pr Cl CF.sub.3 F N CH CH CH t-Bu Cl CF.sub.3 F N CH CH CH Et
Cl CF.sub.3 Me N CH CH CH i-Pr Cl CF.sub.3 Me N CH CH CH t-Bu Cl
CF.sub.3 Me N CH CH CH Et Cl CF.sub.3 CF.sub.3 N CH CH CH i-Pr Cl
CF.sub.3 CF.sub.3 N CH CH CH t-Bu Cl CF.sub.3 CF.sub.3 N CH CH CH
Et Cl CF.sub.3 OMe N CH CH CH i-Pr Cl CF.sub.3 OMe N CH CH CH t-Bu
Cl CF.sub.3 OMe N CH CH CH Et Cl CF.sub.3 CN N CH CH CH i-Pr Cl
CF.sub.3 CN N CH CH CH t-Bu Cl CF.sub.3 CN CH N CH N Et Me CF.sub.3
Cl CH N CH N i-Pr Me CF.sub.3 Cl CH N CH N t-Bu Me CF.sub.3 Cl CH N
CH N Et Me CF.sub.3 Br CH N CH N i-Pr Me CF.sub.3 Br CH N CH N t-Bu
Me CF.sub.3 Br CH N CH N Et Me CF.sub.3 I CH N CH N i-Pr Me
CF.sub.3 I CH N CH N t-Bu Me CF.sub.3 I CH N CH N Et Me CF.sub.3 F
CH N CH N i-Pr Me CF.sub.3 F CH N CH N t-Bu Me CF.sub.3 F CH N CH N
Et Me CF.sub.3 Me CH N CH N i-Pr Me CF.sub.3 Me CH N CH N t-Bu Me
CF.sub.3 Me CH N CH N Et Me CF.sub.3 CF.sub.3 CH N CH N i-Pr Me
CF.sub.3 CF.sub.3 CH N CH N t-Bu Me CF.sub.3 CF.sub.3 CH N CH N Et
Me CF.sub.3 OMe CH N CH N i-Pr Me CF.sub.3 OMe CH N CH N t-Bu Me
CF.sub.3 OMe CH N CH N Et Me CF.sub.3 CN CH N CH N i-Pr Me CF.sub.3
CN CH N CH N t-Bu Me CF.sub.3 CN CH N CH N Et Cl CF.sub.3 Cl CH N
CH N i-Pr Cl CF.sub.3 Cl CH N CH N t-Bu Cl CF.sub.3 Cl CH N CH N Et
Cl CF.sub.3 Br CH N CH N i-Pr Cl CF.sub.3 Br CH N CH N t-Bu Cl
CF.sub.3 Br CH N CH N Et Cl CF.sub.3 I CH N CH N i-Pr Cl CF.sub.3 I
CH N CH N t-Bu Cl CF.sub.3 I CH N CH N Et Cl CF.sub.3 F CH N CH N
i-Pr Cl CF.sub.3 F CH N CH N t-Bu Cl CF.sub.3 F CH N CH N Et Cl
CF.sub.3 Me CH N CH N i-Pr Cl CF.sub.3 Me CH N CH N t-Bu Cl
CF.sub.3 Me CH N CH N Et Cl CF.sub.3 CF.sub.3 CH N CH N i-Pr Cl
CF.sub.3 CF.sub.3 CH N CH N t-Bu Cl CF.sub.3 CF.sub.3 CH N CH N Et
Cl CF.sub.3 OMe CH N CH N i-Pr Cl CF.sub.3 OMe CH N CH N t-Bu Cl
CF.sub.3 OMe CH N CH N Et Cl CF.sub.3 CN CH N CH N i-Pr Cl CF.sub.3
CN CH N CH N t-Bu Cl CF.sub.3 CN CH CH CH CCl Et Me CF.sub.3 Cl CH
CH CH CCl i-Pr Me CF.sub.3 Cl CH CH CH CCl t-Bu Me CF.sub.3 Cl CH
CH CH CCl Et Me CF.sub.3 Br CH CH CH CCl i-Pr Me CF.sub.3 Br CH CH
CH CCl t-Bu Me CF.sub.3 Br CH CH CH CCl Et Me CF.sub.3 I CH CH CH
CCl i-Pr Me CF.sub.3 I CH CH CH CCl t-Bu Me CF.sub.3 I CH CH CH CCl
Et Me CF.sub.3 F CH CH CH CCl i-Pr Me CF.sub.3 F CH CH CR CCl t-Bu
Me CF.sub.3 F CH CH CH CCl Et Me CF.sub.3 Me CH CH CH CCl i-Pr Me
CF.sub.3 Me CH CH CH CCl t-Bu Me CF.sub.3 Me CH CH CH CCl Et Me
CF.sub.3 CF.sub.3 CH CH CH CCl i-Pr Me CF.sub.3 CF.sub.3 CH CH CH
CCl t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CCl Et Me CF.sub.3 OMe CH CH
CH CCl i-Pr Me CF.sub.3 OMe CH CH CH CCl t-Bu Me CF.sub.3 OMe CH CH
CH CCl Et Me CF.sub.3 CN CH CH CH CCl i-Pr Me CF.sub.3 CN CH CH CH
CCl t-Bu Me CF.sub.3 CN CH CH CH CCl Et Cl CF.sub.3 Cl CH CH CH CCl
i-Pr Cl CF.sub.3 Cl CH CH CH CCl t-Bu Cl CF.sub.3 Cl CH CH CH CCl
Et Cl CF.sub.3 Br CH CH CH CCl i-Pr Cl CF.sub.3 Br CH CH CH CCl
t-Bu Cl CF.sub.3 Br CH CH CH CCl Et Cl CF.sub.3 I CH CH CH CCl i-Pr
Cl CF.sub.3 I CH CH CH CCl t-Bu Cl CF.sub.3 I CH CH CH CCl Et Cl
CF.sub.3 F CH CH CH CCl i-Pr Cl CF.sub.3 F CH CH CH CCl t-Bu Cl
CF.sub.3 F CH CH CH CCl Et Cl CF.sub.3 Me CH CH CH CCl i-Pr Cl
CF.sub.3 Me CH CH CH CCl t-Bu Cl CF.sub.3 Me CH CH CH CCl Et Cl
CF.sub.3 CF.sub.3 CH CH CH CCl i-Pr Cl CF.sub.3 CF.sub.3 CH CH CH
CCl t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CCl Et Cl CF.sub.3 OMe CH CH
CH CCl i-Pr Cl CF.sub.3 OMe CH CH CH CCl t-Bu Cl CF.sub.3 OMe CH CH
CH CCl Et Cl CF.sub.3 CN CH CH CH CCl i-Pr Cl CF.sub.3 CN CH CH CH
CCl t-Bu Cl CF.sub.3 CN CH CH CH CF Et Me CF.sub.3 Cl CH CH CH CF
i-Pr Me CF.sub.3 Cl CH CH CH CF t-Bu Me CF.sub.3 Cl CH CH CH CF Et
Me CF.sub.3 Br CH CH CH CF i-Pr Me CF.sub.3 Br CH CH CH CF t-Bu Me
CF.sub.3 Br CH CH CH CF Et Me CF.sub.3 I CH CH CH CF i-Pr Me
CF.sub.3 I CH CH CH CF t-Bu Me CF.sub.3 I CH CH CH CF Et Me
CF.sub.3 F CH CH CH CF i-Pr Me CF.sub.3 F CH CH CH CF t-Bu Me
CF.sub.3 F CH CH CH CF Et Me CF.sub.3 Me CH CH CH CF i-Pr Me
CF.sub.3 Me CH CH CH CF t-Bu Me CF.sub.3 Me CH CH CH CF Et Me
CF.sub.3 CF.sub.3 CH CH CH CF i-Pr Me CF.sub.3 CF.sub.3 CH CH CH CF
t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CF Et Me CF.sub.3 OMe CH CH CH
CF i-Pr Me CF.sub.3 OMe CH CH CH CF t-Bu Me CF.sub.3 OMe CH CH CH
CF Et Me CF.sub.3 CN CH CH CH CF i-Pr Me CF.sub.3 CN CH CH CH CF
t-Bu Me CF.sub.3 CN CH CH CH CF Et Cl CF.sub.3 Cl CH CH CH CF i-Pr
Cl CF.sub.3 Cl CH CH CH CF t-Bu Cl CF.sub.3 Cl CH CH CH CF Et Cl
CF.sub.3 Br CH CH CH CF i-Pr Cl CF.sub.3 Br CH CH CH CF t-Bu Cl
CF.sub.3 Br CH CH CH CF Et Cl CF.sub.3 I CH CH CH CF i-Pr Cl
CF.sub.3 I CH CH CH CF t-Bu Cl CF.sub.3 I CH CH CH CF i-Pr Cl
CF.sub.3 F CH CH CH CF t-Bu Cl CF.sub.3 F CH CH CH CF Et Cl
CF.sub.3 Me CH CH CH CF i-Pr Cl CF.sub.3 Me CH CH CH CF t-Bu Cl
CF.sub.3 Me CH CH CH CF Et Cl CF.sub.3 CF.sub.3 CH CH CH CF i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH CF t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CF
Et Cl CF.sub.3 OMe CH CH CH CF i-Pr Cl CF.sub.3 OMe CH CH CH CF
t-Bu Cl CF.sub.3 OMe CH CH CH CF Et Cl CF.sub.3 CN CH CH CH CF i-Pr
Cl CF.sub.3 CN CH CH CH CF t-Bu Cl CF.sub.3 CN CH CH CH CH Et Me
C.sub.2F.sub.5 Cl CH CH CH CH i-Pr Me C.sub.2F.sub.5 Cl CH CH CH CH
t-Bu Me C.sub.2F.sub.5 Cl CH CH CH CH Et Me C.sub.2F.sub.5 Br CH CH
CH CH i-Pr Me C.sub.2F.sub.5 Br CH CH CH CH t-Bu Me C.sub.2F.sub.5
Br CH CH CH CH Et Me C.sub.2F.sub.5 I CH CH CH CH i-Pr Me
C.sub.2F.sub.5 I CH CH CH CH t-Bu Me C.sub.2F.sub.5 I CH CH CH CH
Et Me C.sub.2F.sub.5 F CH CH CH CH i-Pr Me C.sub.2F.sub.5 F CH CH
CH CH t-Bu Me C.sub.2F.sub.5 F CH CH CH CH Et Me C.sub.2F.sub.5 Me
CH CH CH CH i-Pr Me C.sub.2F.sub.5 Me CH CH CH CH t-Bu Me
C.sub.2F.sub.5 Me CH CH CH CH Et Me C.sub.2F.sub.5 CF.sub.3 CH CH
CH CH i-Pr Me C.sub.2F.sub.5 CF.sub.3 CH CH CH CH t-Bu Me
C.sub.2F.sub.5 CF.sub.3 CH CH CH CH Et Me C.sub.2F.sub.5 OMe CH CH
CH CH i-Pr Me C.sub.2F.sub.5 OMe CH CH CH CH t-Bu Me C.sub.2F.sub.5
OMe CH CH CH CH Et Me C.sub.2F.sub.5 CN CH CH CH CH i-Pr Me
C.sub.2F.sub.5 CN CH CH CH CH t-Bu Me C.sub.2F.sub.5 CN CH CH CH CH
Et Cl C.sub.2F.sub.5 Cl CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Cl CH CH
CH CH t-Bu Cl C.sub.2F.sub.5 Cl CH CH CH CH Et Cl C.sub.2F.sub.5 Br
CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Br CH CH CH CH t-Bu Cl
C.sub.2F.sub.5 Br CH CH CH CH Et Cl C.sub.2F.sub.5 I CH CH CH CH
i-Pr Cl C.sub.2F.sub.5 I CH CH CH CH t-Bu Cl C.sub.2F.sub.5 I CH CH
CH CH Et Cl C.sub.2F.sub.5 F CH CH CH CH i-Pr Cl C.sub.2F.sub.5 F
CH CH CH CH t-Bu Cl C.sub.2F.sub.5 F CH CH CH CH Et Cl
C.sub.2F.sub.5 Me CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Me CH CH CH CH
t-Bu Cl C.sub.2F.sub.5 Me CH CH CH CH Et Cl C.sub.2F.sub.5 CF.sub.3
CH CH CH CH i-Pr Cl C.sub.2F.sub.5 CF.sub.3 CH CH CH CH t-Bu Cl
C.sub.2F.sub.5 CF.sub.3 CH CH CH CH Et Cl C.sub.2F.sub.5 OMe CH CH
CH CH i-Pr Cl C.sub.2F.sub.5 OMe CH CH CH CH t-Bu Cl C.sub.2F.sub.5
OMe CH CH CH CH Et Cl C.sub.2F.sub.5 CN CH CH CH CH i-Pr Cl
C.sub.2F.sub.5 CN CH CH CH CH t-Bu Cl C.sub.2F.sub.5 CN
[0351]
15TABLE 15 54 W X Y Z R.sup.3 R.sup.4 R.sup.7 R.sup.8 CH CH CH CH
Et Me CF.sub.3 Cl CH CH CH CH i-Pr Me CF.sub.3 Cl CH CH CH CH t-Bu
Me CF.sub.3 Cl CH CH CH CH Et Me CF.sub.3 Br CH CH CH CH i-Pr Me
CF.sub.3 Br CH CH CH CH t-Bu Me CF.sub.3 Br CH CH CH CH Et Me
CF.sub.3 I CH CH CH CH i-Pr Me CF.sub.3 I CH CH CH CH t-Bu Me
CF.sub.3 I CH CH CH CH Et Me CF.sub.3 F CH CH CH CH i-Pr Me
CF.sub.3 F CH CH CH CH t-Bu Me CF.sub.3 F CH CH CH CH Et Me
CF.sub.3 Me CH CH CH CH i-Pr Me CF.sub.3 Me CH CH CH CH t-Bu Me
CF.sub.3 Me CH CH CH CH Et Me CF.sub.3 CF.sub.3 CH CH CH CH i-Pr Me
CF.sub.3 CF.sub.3 CH CH CH CH t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CH
Et Me CF.sub.3 OMe CH CH CH CH i-Pr Me CF.sub.3 OMe CH CH CH CH
t-Bu Me CF.sub.3 OMe CH CH CH CH Et Me CF.sub.3 CN CH CH CH CH i-Pr
Me CF.sub.3 CN CH CH CH CH t-Bu Me CF.sub.3 CN CH CH CH CH Et Cl
CF.sub.3 Cl CH CH CH CH i-Pr Cl CF.sub.3 Cl CH CH CH CH t-Bu Cl
CF.sub.3 Cl CH CH CH CH Et Cl CF.sub.3 Br CH CH CH CH i-Pr Cl
CF.sub.3 Br CH CH CH CH t-Bu Cl CF.sub.3 Br CH CH CH CH Et Cl
CF.sub.3 I CH CH CH CH i-Pr Cl CF.sub.3 I CH CH CH CH t-Bu Cl
CF.sub.3 I CH CH CH CH Et Cl CF.sub.3 F CH CH CH CH i-Pr Cl
CF.sub.3 F CH CH CH CH t-Bu Cl CF.sub.3 F CH CH CH CH Et Cl
CF.sub.3 Me CH CH CH CH i-Pr Cl CF.sub.3 Me CH CH CH CH t-Bu Cl
CF.sub.3 Me CH CH CH CH Et Cl CF.sub.3 CF.sub.3 CH CH CH CH i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH CH t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CH
Et Cl CF.sub.3 OMe CH CH CH CH i-Pr Cl CF.sub.3 OMe CH CH CH CH
t-Bu Cl CF.sub.3 OMe CH CH CH CH Et Cl CF.sub.3 CN CH CH CH CH i-Pr
Cl CF.sub.3 CN CH CH CH CH t-Bu Cl CF.sub.3 CN CH CH CH N Et Me
CF.sub.3 Cl CH CH CH N i-Pr Me CF.sub.3 Cl CH CH CH N t-Bu Me
CF.sub.3 Cl CH CH CH N Et Me CF.sub.3 Br CH CH CH N i-Pr Me
CF.sub.3 Br CH CH CH N t-Bu Me CF.sub.3 Br CH CH CH N Et Me
CF.sub.3 I CH CH CH N i-Pr Me CF.sub.3 I CH CH CH N t-Bu Me
CF.sub.3 I CH CH CH N Et Me CF.sub.3 F CH CH CH N i-Pr Me CF.sub.3
F CH CH CH N t-Bu Me CF.sub.3 F CH CH CH N Et Me CF.sub.3 Me CH CH
CH N i-Pr Me CF.sub.3 Me CH CH CH N t-Bu Me CF.sub.3 Me CH CH CH N
Et Me CF.sub.3 CF.sub.3 CH CH CH N i-Pr Me CF.sub.3 CF.sub.3 CH CH
CH N t-Bu Me CF.sub.3 CF.sub.3 CH CH CH N Et Me CF.sub.3 OMe CH CH
CH N i-Pr Me CF.sub.3 OMe CH CH CH N t-Bu Me CF.sub.3 OMe CH CH CH
N Et Me CF.sub.3 CN CH CH CH N i-Pr Me CF.sub.3 CN CH CH CH N t-Bu
Me CF.sub.3 CN CH CH CH N Et Cl CF.sub.3 Cl CH CH CH N i-Pr Cl
CF.sub.3 Cl CH CH CH N t-Bu Cl CF.sub.3 Cl CH CH CH N Et Cl
CF.sub.3 Br CH CH CH N i-Pr Cl CF.sub.3 Br CH CH CH N t-Bu Cl
CF.sub.3 Br CH CH CH N Et Cl CF.sub.3 I CH CH CH N i-Pr Cl CF.sub.3
I CH CH CH N t-Bu Cl CF.sub.3 I CH CH CH N Et Cl CF.sub.3 F CH CH
CH N i-Pr Cl CF.sub.3 F CH CH CH N t-Bu Cl CF.sub.3 F CH CH CH N Et
Cl CF.sub.3 Me CH CH CH N i-Pr Cl CF.sub.3 Me CH CH CH N t-Bu Cl
CF.sub.3 Me CH CH CH N Et Cl CF.sub.3 CF.sub.3 CH CH CH N i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH N t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH N
Et Cl CF.sub.3 OMe CH CH CH N i-Pr Cl CF.sub.3 OMe CH CH CH N t-Bu
Cl CF.sub.3 OMe CH CH CH N Et Cl CF.sub.3 CN CH CH CH N i-Pr Cl
CF.sub.3 CN CH CH CH N t-Bu Cl CF.sub.3 CN CH CH N CH Et Me
CF.sub.3 Cl CH CH N CH i-Pr Me CF.sub.3 Cl CH CH N CH t-Bu Me
CF.sub.3 Cl CH CH N CH Et Me CF.sub.3 Br CH CH N CH i-Pr Me
CF.sub.3 Br CH CH N CH t-Bu Me CF.sub.3 Br CH CH N CH Et Me
CF.sub.3 I CH CH N CH i-Pr Me CF.sub.3 I CH CH N CH t-Bu Me
CF.sub.3 I CH CH N CH Et Me CF.sub.3 F CH CH N CH i-Pr Me CF.sub.3
F CH CH N CH t-Bu Me CF.sub.3 F CH CH N CH Et Me CF.sub.3 Me CH CH
N CH i-Pr Me CF.sub.3 Me CH CH N CH t-Bu Me CF.sub.3 Me CH CH N CH
Et Me CF.sub.3 CF.sub.3 CH CH N CH i-Pr Me CF.sub.3 CF.sub.3 CH CH
N CH t-Bu Me CF.sub.3 CF.sub.3 CH CH N CH Et Me CF.sub.3 OMe CH CH
N CH i-Pr Me CF.sub.3 OMe CH CH N CH t-Bu Me CF.sub.3 OMe CH CH N
CH Et Me CF.sub.3 CN CH CH N CH i-Pr Me CF.sub.3 CN CH CH N CH t-Bu
Me CF.sub.3 CN CH CH N CH Et Cl CF.sub.3 Cl CH CH N CH i-Pr Cl
CF.sub.3 Cl CH CH N CH t-Bu Cl CF.sub.3 Cl CH CH N CH Et Cl
CF.sub.3 Br CH CH N CH i-Pr Cl CF.sub.3 Br CH CH N CH t-Bu Cl
CF.sub.3 Br CH CH N CH Et Cl CF.sub.3 I CH CH N CH i-Pr Cl CF.sub.3
I CH CH N CH t-Bu Cl CF.sub.3 I CH CH N CH Et Cl CF.sub.3 F CH CH N
CH i-Pr Cl CF.sub.3 F CH CH N CH t-Bu Cl CF.sub.3 F CH CH N CH Et
Cl CF.sub.3 Me CH CH N CH i-Pr Cl CF.sub.3 Me CH CH N CH t-Bu Cl
CF.sub.3 Me CH CH N CH Et Cl CF.sub.3 CF.sub.3 CH CH N CH i-Pr Cl
CF.sub.3 CF.sub.3 CH CH N CH t-Bu Cl CF.sub.3 CF.sub.3 CH CH N CH
Et Cl CF.sub.3 OMe CH CH N CH i-Pr Cl CF.sub.3 OMe CH CH N CH t-Bu
Cl CF.sub.3 OMe CH CH N CH Et Cl CF.sub.3 CN CH CH N CH i-Pr Cl
CF.sub.3 CN CH CH N CH t-Bu Cl CF.sub.3 CN CH N CH CH Et Me
CF.sub.3 Cl CH N CH CH i-Pr Me CF.sub.3 Cl CH N CH CH t-Bu Me
CF.sub.3 Cl CH N CH CH Et Me CF.sub.3 Br CH N CH CH i-Pr Me
CF.sub.3 Br CH N CH CH t-Bu Me CF.sub.3 Br CH N CH CH Et Me
CF.sub.3 I CH N CH CH i-Pr Me CF.sub.3 I CH N CH CH t-Bu Me
CF.sub.3 I CH N CH CH Et Me CF.sub.3 F CH N CH CH i-Pr Me CF.sub.3
F CH N CH CH t-Bu Me CF.sub.3 F CH N CH CH Et Me CF.sub.3 Me CH N
CH CH i-Pr Me CF.sub.3 Me CH N CH CH t-Bu Me CF.sub.3 Me CH N CH CH
Et Me CF.sub.3 CF.sub.3 CH N CH CH i-Pr Me CF.sub.3 CF.sub.3 CH N
CH CH t-Bu Me CF.sub.3 CF.sub.3 CH N CH CH Et Me CF.sub.3 OMe CH N
CH CH i-Pr Me CF.sub.3 OMe CH N CH CH t-Bu Me CF.sub.3 OMe CH N CH
CH Et Me CF.sub.3 CN CH N CH CH i-Pr Me CF.sub.3 CN CH N CH CH t-Bu
Me CF.sub.3 CN CH N CH CH Et Cl CF.sub.3 Cl CH N CH CH i-Pr Cl
CF.sub.3 Cl CH N CH CH t-Bu Cl CF.sub.3 Cl CH N CH CH Et Cl
CF.sub.3 Br CH N CH CH i-Pr Cl CF.sub.3 Br CH N CH CH t-Bu Cl
CF.sub.3 Br CH N CH CH Et Cl CF.sub.3 I CH N CH CH i-Pr Cl CF.sub.3
I CH N CH CH t-Bu Cl CF.sub.3 I CH N CH CH Et Cl CF.sub.3 F CH N CH
CH i-Pr Cl CF.sub.3 F CH N CH CH t-Bu Cl CF.sub.3 F CH N CH CH Et
Cl CF.sub.3 Me CH N CH CH i-Pr Cl CF.sub.3 Me CH N CH CH t-Bu Cl
CF.sub.3 Me CH N CH CH Et Cl CF.sub.3 CF.sub.3 CH N CH CH i-Pr Cl
CF.sub.3 CF.sub.3 CH N CH CH t-Bu Cl CF.sub.3 CF.sub.3 CH N CH CH
Et Cl CF.sub.3 OMe CH N CH CH i-Pr Cl CF.sub.3 OMe CH N CH CH t-Bu
Cl CF.sub.3 OMe CH N CH CH Et Cl CF.sub.3 CN CH N CH CH i-Pr Cl
CF.sub.3 CN CH N CH CH t-Bu Cl CF.sub.3 CN N CH CH CH Et Me
CF.sub.3 Cl N CH CH CH i-Pr Me CF.sub.3 Cl N CH CH CH t-Bu Me
CF.sub.3 Cl N CH CH CH Et Me CF.sub.3 Br N CH CH CH i-Pr Me
CF.sub.3 Br N CH CH CH t-Bu Me CF.sub.3 Br N CH CH CH Et Me
CF.sub.3 I N CH CH CH i-Pr Me CF.sub.3 I N CH CH CH t-Bu Me
CF.sub.3 I N CH CH CH Et Me CF.sub.3 F N CH CH CH i-Pr Me CF.sub.3
F N CH CH CH t-Bu Me CF.sub.3 F N CH CH CH Et Me CF.sub.3 Me N CH
CH CH i-Pr Me CF.sub.3 Me N CH CH CH t-Bu Me CF.sub.3 Me N CH CH CH
Et Me CF.sub.3 CF.sub.3 N CH CH CH i-Pr Me CF.sub.3 CF.sub.3 N CH
CH CH t-Bu Me CF.sub.3 CF.sub.3 N CH CH CH Et Me CF.sub.3 OMe N CH
CH CH i-Pr Me CF.sub.3 OMe N CH CH CH t-Bu Me CF.sub.3 OMe N CH CH
CH Et Me CF.sub.3 CN N CH CH CH i-Pr Me CF.sub.3 CN N CH CH CH t-Bu
Me CF.sub.3 CN N CH CH CH Et Cl CF.sub.3 Cl N CH CH CH i-Pr Cl
CF.sub.3 Cl N CH CH CH t-Bu Cl CF.sub.3 Cl N CH CH CH Et Cl
CF.sub.3 Br N CH CH CH i-Pr Cl CF.sub.3 Br N CH CH CH t-Bu Cl
CF.sub.3 Br N CH CH CH Et Cl CF.sub.3 I N CH CH CH i-Pr Cl CF.sub.3
I N CH CH CH t-Bu Cl CF.sub.3 I N CH CH CH Et Cl CF.sub.3 F N CH CH
CH i-Pr Cl CF.sub.3 F N CH CH CH t-Bu Cl CF.sub.3 F N CH CH CH Et
Cl CF.sub.3 Me N CH CH CH i-Pr Cl CF.sub.3 Me N CH CH CH t-Bu Cl
CF.sub.3 Me N CH CH CH Et Cl CF.sub.3 CF.sub.3 N CH CH CH i-Pr Cl
CF.sub.3 CF.sub.3 N CH CH CH t-Bu Cl CF.sub.3 CF.sub.3 N CH CH CH
Et Cl CF.sub.3 OMe N CH CH CH i-Pr Cl CF.sub.3 OMe N CH CH CH t-Bu
Cl CF.sub.3 OMe N CH CH CH Et Cl CF.sub.3 CN N CH CH CH i-Pr Cl
CF.sub.3 CN N CH CH CH t-Bu Cl CF.sub.3 CN CH N CH N Et Me CF.sub.3
Cl CH N CH N i-Pr Me CF.sub.3 Cl CH N CH N t-Bu Me CF.sub.3 Cl CH N
CH N Et Me CF.sub.3 Br CH N CH N i-Pr Me CF.sub.3 Br CH N CH N t-Bu
Me CF.sub.3 Br CH N CH N Et Me CF.sub.3 I CH N CH N i-Pr Me
CF.sub.3 I CH N CH N t-Bu Me CF.sub.3 I CH N CH N Et Me CF.sub.3 F
CH N CH N i-Pr Me CF.sub.3 F CH N CH N t-Bu Me CF.sub.3 F CH N CH N
Et Me CF.sub.3 Me CH N CH N i-Pr Me CF.sub.3 Me CH N CH N t-Bu Me
CF.sub.3 Me CH N CH N Et Me CF.sub.3 CF.sub.3 CH N CH N i-Pr Me
CF.sub.3 CF.sub.3 CH N CH N t-Bu Me CF.sub.3 CF.sub.3 CH N CH N Et
Me CF.sub.3 OMe CH N CH N i-Pr Me CF.sub.3 OMe CH N CH N t-Bu Me
CF.sub.3 OMe CH N CH N Et Me CF.sub.3 CN CH N CH N i-Pr Me CF.sub.3
CN CH N CH N t-Bu Me CF.sub.3 CN CH N CH N Et Cl CF.sub.3 Cl CH N
CH N i-Pr Cl CF.sub.3 Cl CH N CH N t-Bu Cl CF.sub.3 Cl CH N CH N Et
Cl CF.sub.3 Br CH N CH N i-Pr Cl CF.sub.3 Br CH N CH N t-Bu Cl
CF.sub.3 Br CH N CH N Et Cl CF.sub.3 I CH N CH N i-Pr Cl CF.sub.3 I
CH N CH N t-Bu Cl CF.sub.3 I CH N CH N Et Cl CF.sub.3 F CH N CH N
i-Pr Cl CF.sub.3 F CH N CH N t-Bu Cl CF.sub.3 F CH N CH N Et Cl
CF.sub.3 Me CH N CH N i-Pr Cl CF.sub.3 Me CH N CH N t-Bu Cl
CF.sub.3 Me CH N CH N Et Cl CF.sub.3 CF.sub.3 CH N CH N i-Pr Cl
CF.sub.3 CF.sub.3 CH N CH N t-Bu Cl CF.sub.3 CF.sub.3 CH N CH N Et
Cl CF.sub.3 OMe CH N CH N i-Pr Cl CF.sub.3 OMe CH N CH N t-Bu Cl
CF.sub.3 OMe CH N CH N Et Cl CF.sub.3 CN CH N CH N i-Pr Cl CF.sub.3
CN CH N CH N t-Bu Cl CF.sub.3 CN CH CH CH CCl Et Me CF.sub.3 Cl CH
CH CH CCl i-Pr Me CF.sub.3 Cl CH CH CH CCl t-Bu Me CF.sub.3 Cl CH
CH CH CCl Et Me CF.sub.3 Br CH CH CH CCl i-Pr Me CF.sub.3 Br CH CH
CH CCl t-Bu Me CF.sub.3 Br CH CH CH CCl Et Me CF.sub.3 I CH CH CH
CCl i-Pr Me CF.sub.3 I CH CH CH CCl t-Bu Me CF.sub.3 I CH CH CH CCl
Et Me CF.sub.3 F CH CH CH CCl i-Pr Me CF.sub.3 F CH CH CH CCl t-Bu
Me CF.sub.3 F CH CH CH CCl Et Me CF.sub.3 Me CH CH CH CCl i-Pr Me
CF.sub.3 Me CH CH CH CCl t-Bu Me CF.sub.3 Me CH CH CH CCl Et Me
CF.sub.3 CF.sub.3 CH CH CH CCl i-Pr Me CF.sub.3 CF.sub.3 CH CH CH
CCl t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CCl Et Me CF.sub.3 OMe CH CH
CH CCl i-Pr Me CF.sub.3 OMe CH CH CH CCl t-Bu Me CF.sub.3 OMe CH CH
CH CCl Et Me CF.sub.3 CN CH CH CH CCl i-Pr Me CF.sub.3 CN CH CH CH
CCl t-Bu Me CF.sub.3 CN CH CH CH CCl Et Cl CF.sub.3 Cl CH CH CH CCl
i-Pr Cl CF.sub.3 Cl CH CH CH CCl t-Bu Cl CF.sub.3 Cl CH CH CH CCl
Et Cl CF.sub.3 Br CH CH CH CCl i-Pr Cl CF.sub.3 Br CH CH CH CCl
t-Bu Cl CF.sub.3 Br CH CH CH CCl Et Cl CF.sub.3 I CH CH CH CCl i-Pr
Cl CF.sub.3 I CH CH CH CCl t-Bu Cl CF.sub.3 I CH CH CH CCl Et Cl
CF.sub.3 F CH CH CH CCl i-Pr Cl CF.sub.3 F CH CH CH CCl t-Bu Cl
CF.sub.3 F CH CH CH CCl Et Cl CF.sub.3 Me CH CH CH CCl i-Pr Cl
CF.sub.3 Me CH CH CH CCl t-Bu Cl CF.sub.3 Me CH CH CH CCl Et Cl
CF.sub.3 CF.sub.3 CH CH CH CCl i-Pr Cl CF.sub.3 CF.sub.3 CH CH CH
CCl t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CCl Et Cl CF.sub.3 OMe CH CH
CH CCl i-Pr Cl CF.sub.3 OMe CH CH CH CCl t-Bu Cl CF.sub.3 OMe CH CH
CH CCl Et Cl CF.sub.3 CN CH CH CH CCl i-Pr Cl CF.sub.3 CN CH CH CH
CCl t-Bu Cl CF.sub.3 CN CH CH CH CF Et Me CF.sub.3 Cl CH CH CH CF
i-Pr Me CF.sub.3 Cl CH CH CH CF t-Bu Me CF.sub.3 Cl CH CH CH CF Et
Me CF.sub.3 Br CH CH CH CF i-Pr Me CF.sub.3 Br CH CH CH CF t-Bu Me
CF.sub.3 Br CH CH CH CF Et Me CF.sub.3 I CH CH CH CF i-Pr Me
CF.sub.3 I CH CH CH CF t-Bu Me CF.sub.3 I CH CH CH CF Et Me
CF.sub.3 F CH CH CH CF i-Pr Me CF.sub.3 F CH CH CH CF t-Bu Me
CF.sub.3 F CH CH CH CF Et Me CF.sub.3 Me CH CH CH CF i-Pr Me
CF.sub.3 Me CH CH CH CF t-Bu Me CF.sub.3 Me CH CH CH CF Et Me
CF.sub.3 CF.sub.3 CH CH CH CF i-Pr Me CF.sub.3 CF.sub.3 CH CH CH CF
t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CF Et Me CF.sub.3 OMe CH CH CH
CF i-Pr Me CF.sub.3 OMe CH CH CH CF t-Bu Me CF.sub.3 OMe CH CH CH
CF Et Me CF.sub.3 CN CH CH CH CF i-Pr Me CF.sub.3 CN CH CH CH CF
t-Bu Me CF.sub.3 CN CH CH CH CF Et Cl CF.sub.3 Cl CH CH CH CF i-Pr
Cl CF.sub.3 Cl CH CH CH CF t-Bu Cl CF.sub.3 Cl CH CH CH CF Et Cl
CF.sub.3 Br CH CH CH CF i-Pr Cl CF.sub.3 Br CH CH CH CF t-Bu Cl
CF.sub.3 Br CH CH CH CF Et Cl CF.sub.3 I CH CH CH CF i-Pr Cl
CF.sub.3 I CH CH CH CF t-Bu Cl CF.sub.3 I CH CH CH CF i-Pr Cl
CF.sub.3 F CH CH CH CF t-Bu Cl CF.sub.3 F CH CH CH CF Et Cl
CF.sub.3 Me CH CH CH CF i-Pr Cl CF.sub.3 Me CH CH CH CF t-Bu Cl
CF.sub.3 Me CH CH CH CF Et Cl CF.sub.3 CF.sub.3 CH CH CH CF i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH CF t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CF
Et Cl CF.sub.3 OMe CH CH CH CF i-Pr Cl CF.sub.3 OMe CH CH CH CF
t-Bu Cl CF.sub.3 OMe CH CH CH CF Et Cl CF.sub.3 CN CH CH CH CF i-Pr
Cl CF.sub.3 CN CH CH CH CF t-Bu Cl CF.sub.3 CN CH CH CH CH Et Me
C.sub.2F.sub.5 Cl CH CH CH CH i-Pr Me C.sub.2F.sub.5 Cl CH CH CH CH
t-Bu Me C.sub.2F.sub.5 Cl CH CH CH CH Et Me C.sub.2F.sub.5 Br CH CH
CH CH i-Pr Me C.sub.2F.sub.5 Br CH CH CH CH t-Bu Me C.sub.2F.sub.5
Br CH CH CH CH Et Me C.sub.2F.sub.5 I CH CH CH CH i-Pr Me
C.sub.2F.sub.5 I CH CH CH CH t-Bu Me C.sub.2F.sub.5 I CH CH CH CH
Et Me C.sub.2F.sub.5 F CH CH CH CH i-Pr Me C.sub.2F.sub.5 F CH CH
CH CH t-Bu Me C.sub.2F.sub.5 F CH CH CH CH Et Me C.sub.2F.sub.5 Me
CH CH CH CH i-Pr Me C.sub.2F.sub.5 Me CH CH CH CH t-Bu Me
C.sub.2F.sub.5 Me CH CH CH CH Et Me C.sub.2F.sub.5 CF.sub.3 CH CH
CH CH i-Pr Me C.sub.2F.sub.5 CF.sub.3 CH CH CH CH t-Bu Me
C.sub.2F.sub.5 CF.sub.3 CH CH CH CH Et Me C.sub.2F.sub.5 OMe CH CH
CH CH i-Pr Me C.sub.2F.sub.5 OMe CH CH CH CH t-Bu Me C.sub.2F.sub.5
OMe CH CH CH CH Et Me C.sub.2F.sub.5 CN CH CH CH CH i-Pr Me
C.sub.2F.sub.5 CN CH CH CH CH t-Bu Me C.sub.2F.sub.5 CN CH CH CH CH
Et Cl C.sub.2F.sub.5 Cl CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Cl CH CH
CH CH t-Bu Cl C.sub.2F.sub.5 Cl CH CH CH CH Et Cl C.sub.2F.sub.5 Br
CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Br CH CH CH CH t-Bu Cl
C.sub.2F.sub.5 Br CH CH CH CH Et Cl C.sub.2F.sub.5 I CH CH CH CH
i-Pr Cl C.sub.2F.sub.5 I CH CH CH CH t-Bu Cl C.sub.2F.sub.5 I CH CH
CH CH Et Cl C.sub.2F.sub.5 F CH CH CH CH i-Pr Cl C.sub.2F.sub.5 F
CH CH CH CH t-Bu Cl C.sub.2F.sub.5 F CH CH CH CH Et Cl
C.sub.2F.sub.5 Me CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Me CH CH CH CH
t-Bu Cl C.sub.2F.sub.5 Me CH CH CH CH Et Cl C.sub.2F.sub.5 CF.sub.3
CH CH CH CH i-Pr Cl C.sub.2F.sub.5 CF.sub.3 CH CH CH CH t-Bu Cl
C.sub.2F.sub.5 CF.sub.3 CH CH CH CH Et Cl C.sub.2F.sub.5 OMe CH CH
CH CH i-Pr Cl C.sub.2F.sub.5 OMe CH CH CH CH t-Bu Cl C.sub.2F.sub.5
OMe CH CH CH CH Et Cl C.sub.2F.sub.5 CN CH CH CH CH i-Pr Cl
C.sub.2F.sub.5 CN CH CH CH CH t-Bu Cl C.sub.2F.sub.5 CN
[0352]
16TABLE 16 55 W X Y Z R.sup.3 R.sup.4 R.sup.7 R.sup.8 CH CH CH CH
Et Me CF.sub.3 Cl CH CH CH CH i-Pr Me CF.sub.3 Cl CH CH CH CH t-Bu
Me CF.sub.3 Cl CH CH CH CH Et Me CF.sub.3 Br CH CH CH CH i-Pr Me
CF.sub.3 Br CH CH CH CH t-Bu Me CF.sub.3 Br CH CH CH CH Et Me
CF.sub.3 I CH CH CH CH i-Pr Me CF.sub.3 I CH CH CH CH t-Bu Me
CF.sub.3 I CH CH CH CH Et Me CF.sub.3 F CH CH CH CH i-Pr Me
CF.sub.3 F CH CH CH CH t-Bu Me CF.sub.3 F CH CH CH CH Et Me
CF.sub.3 Me CH CH CH CH i-Pr Me CF.sub.3 Me CH CH CH CH t-Bu Me
CF.sub.3 Me CH CH CH CH Et Me CF.sub.3 CF.sub.3 CH CH CH CH i-Pr Me
CF.sub.3 CF.sub.3 CH CH CH CH t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CH
Et Me CF.sub.3 OMe CH CH CH CH i-Pr Me CF.sub.3 OMe CH CH CH CH
t-Bu Me CF.sub.3 OMe CH CH CH CH Et Me CF.sub.3 CN CH CH CH CH i-Pr
Me CF.sub.3 CN CH CH CH CH t-Bu Me CF.sub.3 CN CH CH CH CH Et Cl
CF.sub.3 Cl CH CH CH CH i-Pr Cl CF.sub.3 Cl CH CH CH CH t-Bu Cl
CF.sub.3 Cl CH CH CH CH Et Cl CF.sub.3 Br CH CH CH CH i-Pr Cl
CF.sub.3 Br CH CH CH CH t-Bu Cl CF.sub.3 Br CH CH CH CH Et Cl
CF.sub.3 I CH CH CH CH i-Pr Cl CF.sub.3 I CH CH CH CH t-Bu Cl
CF.sub.3 I CH CH CH CH Et Cl CF.sub.3 F CH CH CH CH i-Pr Cl
CF.sub.3 F CH CH CH CH t-Bu Cl CF.sub.3 F CH CH CH CH Et Cl
CF.sub.3 Me CH CH CH CH i-Pr Cl CF.sub.3 Me CH CH CH CH t-Bu Cl
CF.sub.3 Me CH CH CH CH Et Cl CF.sub.3 CF.sub.3 CH CH CH CH i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH CH t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CH
Et Cl CF.sub.3 OMe CH CH CH CH i-Pr Cl CF.sub.3 OMe CH CH CH CH
t-Bu Cl CF.sub.3 OMe CH CH CH CH Et Cl CF.sub.3 CN CH CH CH CH i-Pr
Cl CF.sub.3 CN CH CH CH CH t-Bu Cl CF.sub.3 CN CH CH CH N Et Me
CF.sub.3 Cl CH CH CH N i-Pr Me CF.sub.3 Cl CH CH CH N t-Bu Me
CF.sub.3 Cl CH CH CH N Et Me CF.sub.3 Br CH CH CH N i-Pr Me
CF.sub.3 Br CH CH CH N t-Bu Me CF.sub.3 Br CH CH CH N Et Me
CF.sub.3 I CH CH CH N i-Pr Me CF.sub.3 I CH CH CH N t-Bu Me
CF.sub.3 I CH CH CH N Et Me CF.sub.3 F CH CH CH N i-Pr Me CF.sub.3
F CH CH CH N t-Bu Me CF.sub.3 F CH CH CH N Et Me CF.sub.3 Me CH CH
CH N i-Pr Me CF.sub.3 Me CH CH CH N t-Bu Me CF.sub.3 Me CH CH CH N
Et Me CF.sub.3 CF.sub.3 CH CH CH N i-Pr Me CF.sub.3 CF.sub.3 CH CH
CH N t-Bu Me CF.sub.3 CF.sub.3 CH CH CH N Et Me CF.sub.3 OMe CH CH
CH N i-Pr Me CF.sub.3 OMe CH CH CH N t-Bu Me CF.sub.3 OMe CH CH CH
N Et Me CF.sub.3 CN CH CH CH N i-Pr Me CF.sub.3 CN CH CH CH N t-Bu
Me CF.sub.3 CN CH CH CH N Et Cl CF.sub.3 Cl CH CH CH N i-Pr Cl
CF.sub.3 Cl CH CH CH N t-Bu Cl CF.sub.3 Cl CH CH CH N Et Cl
CF.sub.3 Br CH CH CH N i-Pr Cl CF.sub.3 Br CH CH CH N t-Bu Cl
CF.sub.3 Br CH CH CH N Et Cl CF.sub.3 I CH CH CH N i-Pr Cl CF.sub.3
I CH CH CH N t-Bu Cl CF.sub.3 I CH CH CH N Et Cl CF.sub.3 F CH CH
CH N i-Pr Cl CF.sub.3 F CH CH CH N t-Bu Cl CF.sub.3 F CH CH CH N Et
Cl CF.sub.3 Me CH CH CH N i-Pr Cl CF.sub.3 Me CH CH CH N t-Bu Cl
CF.sub.3 Me CH CH CH N Et Cl CF.sub.3 CF.sub.3 CH CH CH N i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH N t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH N
Et Cl CF.sub.3 OMe CH CH CH N i-Pr Cl CF.sub.3 OMe CH CH CH N t-Bu
Cl CF.sub.3 OMe CH CH CH N Et Cl CF.sub.3 CN CH CH CH N i-Pr Cl
CF.sub.3 CN CH CH CH N t-Bu Cl CF.sub.3 CN CH CH N CH Et Me
CF.sub.3 Cl CH CH N CH i-Pr Me CF.sub.3 Cl CH CH N CH t-Bu Me
CF.sub.3 Cl CH CH N CH Et Me CF.sub.3 Br CH CH N CH i-Pr Me
CF.sub.3 Br CH CH N CH t-Bu Me CF.sub.3 Br CH CH N CH Et Me
CF.sub.3 I CH CH N CH i-Pr Me CF.sub.3 I CH CH N CH t-Bu Me
CF.sub.3 I CH CH N CH Et Me CF.sub.3 F CH CH N CH i-Pr Me CF.sub.3
F CH CH N CH t-Bu Me CF.sub.3 F CH CH N CH Et Me CF.sub.3 Me CH CH
N CH i-Pr Me CF.sub.3 Me CH CH N CH t-Bu Me CF.sub.3 Me CH CH N CH
Et Me CF.sub.3 CF.sub.3 CH CH N CH i-Pr Me CF.sub.3 CF.sub.3 CH CH
N CH t-Bu Me CF.sub.3 CF.sub.3 CH CH N CH Et Me CF.sub.3 OMe CH CH
N CH i-Pr Me CF.sub.3 OMe CH CH N CH t-Bu Me CF.sub.3 OMe CH CH N
CH Et Me CF.sub.3 CN CH CH N CH i-Pr Me CF.sub.3 CN CH CH N CH t-Bu
Me CF.sub.3 CN CH CH N CH Et Cl CF.sub.3 Cl CH CH N CH i-Pr Cl
CF.sub.3 Cl CH CH N CH t-Bu Cl CF.sub.3 Cl CH CH N CH Et Cl
CF.sub.3 Br CH CH N CH i-Pr Cl CF.sub.3 Br CH CH N CH t-Bu Cl
CF.sub.3 Br CH CH N CH Et Cl CF.sub.3 I CH CH N CH i-Pr Cl CF.sub.3
I CH CH N CH t-Bu Cl CF.sub.3 I CH CH N CH Et Cl CF.sub.3 F CH CH N
CH i-Pr Cl CF.sub.3 F CH CH N CH t-Bu Cl CF.sub.3 F CH CH N CH Et
Cl CF.sub.3 Me CH CH N CH i-Pr Cl CF.sub.3 Me CH CH N CH t-Bu Cl
CF.sub.3 Me CH CH N CH Et Cl CF.sub.3 CF.sub.3 CH CH N CH i-Pr Cl
CF.sub.3 CF.sub.3 CH CH N CH t-Bu Cl CF.sub.3 CF.sub.3 CH CH N CH
Et Cl CF.sub.3 OMe CH CH N CH i-Pr Cl CF.sub.3 OMe CH CH N CH t-Bu
Cl CF.sub.3 OMe CH CH N CH Et Cl CF.sub.3 CN CH CH N CH i-Pr Cl
CF.sub.3 CN CH CH N CH t-Bu Cl CF.sub.3 CN CH N CH CH Et Me
CF.sub.3 Cl CH N CH CH i-Pr Me CF.sub.3 Cl CH N CH CH t-Bu Me
CF.sub.3 Cl CH N CH CH Et Me CF.sub.3 Br CH N CH CH i-Pr Me
CF.sub.3 Br CH N CH CH t-Bu Me CF.sub.3 Br CH N CH CH Et Me
CF.sub.3 I CH N CH CH i-Pr Me CF.sub.3 I CH N CH CH t-Bu Me
CF.sub.3 I CH N CH CH Et Me CF.sub.3 F CH N CH CH i-Pr Me CF.sub.3
F CH N CH CH t-Bu Me CF.sub.3 F CH N CH CH Et Me CF.sub.3 Me CH N
CH CH i-Pr Me CF.sub.3 Me CH N CH CH t-Bu Me CF.sub.3 Me CH N CH CH
Et Me CF.sub.3 CF.sub.3 CH N CH CH i-Pr Me CF.sub.3 CF.sub.3 CH N
CH CH t-Bu Me CF.sub.3 CF.sub.3 CH N CH CH Et Me CF.sub.3 OMe CH N
CH CH i-Pr Me CF.sub.3 OMe CH N CH CH t-Bu Me CF.sub.3 OMe CH N CH
CH Et Me CF.sub.3 CN CH N CH CH i-Pr Me CF.sub.3 CN CH N CH CH t-Bu
Me CF.sub.3 CN CH N CH CH Et Cl CF.sub.3 Cl CH N CH CH i-Pr Cl
CF.sub.3 Cl CH N CH CH t-Bu Cl CF.sub.3 Cl CH N CH CH Et Cl
CF.sub.3 Br CH N CH CH i-Pr Cl CF.sub.3 Br CH N CH CH t-Bu Cl
CF.sub.3 Br CH N CH CH Et Cl CF.sub.3 I CH N CH CH i-Pr Cl CF.sub.3
I CH N CH CH t-Bu Cl CF.sub.3 I CH N CH CH Et Cl CF.sub.3 F CH N CH
CH i-Pr Cl CF.sub.3 F CH N CH CH t-Bu Cl CF.sub.3 F CH N CH CH Et
Cl CF.sub.3 Me CH N CH CH i-Pr Cl CF.sub.3 Me CH N CH CH t-Bu Cl
CF.sub.3 Me CH N CH CH Et Cl CF.sub.3 CF.sub.3 CH N CH CH i-Pr Cl
CF.sub.3 CF.sub.3 CH N CH CH t-Bu Cl CF.sub.3 CF.sub.3 CH N CH CH
Et Cl CF.sub.3 OMe CH N CH CH i-Pr Cl CF.sub.3 OMe CH N CH CH t-Bu
Cl CF.sub.3 OMe CH N CH CH Et Cl CF.sub.3 CN CH N CH CH i-Pr Cl
CF.sub.3 CN CH N CH CH t-Bu Cl CF.sub.3 CN N CH CH CH Et Me
CF.sub.3 Cl N CH CH CH i-Pr Me CF.sub.3 Cl N CH CH CH t-Bu Me
CF.sub.3 Cl N CH CH CH Et Me CF.sub.3 Br N CH CH CH i-Pr Me
CF.sub.3 Br N CH CH CH t-Bu Me CF.sub.3 Br N CH CH CH Et Me
CF.sub.3 I N CH CH CH i-Pr Me CF.sub.3 I N CH CH CH t-Bu Me
CF.sub.3 I N CH CH CH Et Me CF.sub.3 F N CH CH CH i-Pr Me CF.sub.3
F N CH CH CH t-Bu Me CF.sub.3 F N CH CH CH Et Me CF.sub.3 Me N CH
CH CH i-Pr Me CF.sub.3 Me N CH CH CH t-Bu Me CF.sub.3 Me N CH CH CH
Et Me CF.sub.3 CF.sub.3 N CH CH CH i-Pr Me CF.sub.3 CF.sub.3 N CH
CH CH t-Bu Me CF.sub.3 CF.sub.3 N CH CH CH Et Me CF.sub.3 OMe N CH
CH CH i-Pr Me CF.sub.3 OMe N CH CH CH t-Bu Me CF.sub.3 OMe N CH CH
CH Et Me CF.sub.3 CN N CH CH CH i-Pr Me CF.sub.3 CN N CH CH CH t-Bu
Me CF.sub.3 CN N CH CH CH Et Cl CF.sub.3 Cl N CH CH CH i-Pr Cl
CF.sub.3 Cl N CH CH CH t-Bu Cl CF.sub.3 Cl N CH CH CH Et Cl
CF.sub.3 Br N CH CH CH i-Pr Cl CF.sub.3 Br N CH CH CH t-Bu Cl
CF.sub.3 Br N CH CH CH Et Cl CF.sub.3 I N CH CH CH i-Pr Cl CF.sub.3
I N CH CH CH t-Bu Cl CF.sub.3 I N CH CH CH Et Cl CF.sub.3 F N CH CH
CH i-Pr Cl CF.sub.3 F N CH CH CH t-Bu Cl CF.sub.3 F N CH CH CH Et
Cl CF.sub.3 Me N CH CH CH i-Pr Cl CF.sub.3 Me N CH CH CH t-Bu Cl
CF.sub.3 Me N CH CH CH Et Cl CF.sub.3 CF.sub.3 N CH CH CH i-Pr Cl
CF.sub.3 CF.sub.3 N CH CH CH t-Bu Cl CF.sub.3 CF.sub.3 N CH CH CH
Et Cl CF.sub.3 OMe N CH CH CH i-Pr Cl CF.sub.3 OMe N CH CH CH t-Bu
Cl CF.sub.3 OMe N CH CH CH Et Cl CF.sub.3 CN N CH CH CH i-Pr Cl
CF.sub.3 CN N CH CH CH t-Bu Cl CF.sub.3 CN CH N CH N Et Me CF.sub.3
Cl CH N CH N i-Pr Me CF.sub.3 Cl CH N CH N t-Bu Me CF.sub.3 Cl CH N
CH N Et Me CF.sub.3 Br CH N CH N i-Pr Me CF.sub.3 Br CH N CH N t-Bu
Me CF.sub.3 Br CH N CH N Et Me CF.sub.3 I CH N CH N i-Pr Me
CF.sub.3 I CH N CH N t-Bu Me CF.sub.3 I CH N CH N Et Me CF.sub.3 F
CH N CH N i-Pr Me CF.sub.3 F CH N CH N t-Bu Me CF.sub.3 F CH N CH N
Et Me CF.sub.3 Me CH N CH N i-Pr Me CF.sub.3 Me CH N CH N t-Bu Me
CF.sub.3 Me CH N CH N Et Me CF.sub.3 CF.sub.3 CH N CH N i-Pr Me
CF.sub.3 CF.sub.3 CH N CH N t-Bu Me CF.sub.3 CF.sub.3 CH N CH N Et
Me CF.sub.3 OMe CH N CH N i-Pr Me CF.sub.3 OMe CH N CH N t-Bu Me
CF.sub.3 OMe CH N CH N Et Me CF.sub.3 CN CH N CH N i-Pr Me CF.sub.3
CN CH N CH N t-Bu Me CF.sub.3 CN CH N CH N Et Cl CF.sub.3 Cl CH N
CH N i-Pr Cl CF.sub.3 Cl CH N CH N t-Bu Cl CF.sub.3 Cl CH N CH N Et
Cl CF.sub.3 Br CH N CH N i-Pr Cl CF.sub.3 Br CH N CH N t-Bu Cl
CF.sub.3 Br CH N CH N Et Cl CF.sub.3 I CH N CH N i-Pr Cl CF.sub.3 I
CH N CH N t-Bu Cl CF.sub.3 I CH N CH N Et Cl CF.sub.3 F CH N CH N
i-Pr Cl CF.sub.3 F CH N CH N t-Bu Cl CF.sub.3 F CH N CH N Et Cl
CF.sub.3 Me CH N CH N i-Pr Cl CF.sub.3 Me CH N CH N t-Bu Cl
CF.sub.3 Me CH N CH N Et Cl CF.sub.3 CF.sub.3 CH N CH N i-Pr Cl
CF.sub.3 CF.sub.3 CH N CH N t-Bu Cl CF.sub.3 CF.sub.3 CH N CH N Et
Cl CF.sub.3 OMe CH N CH N i-Pr Cl CF.sub.3 OMe CH N CH N t-Bu Cl
CF.sub.3 OMe CH N CH N Et Cl CF.sub.3 CN CH N CH N i-Pr Cl CF.sub.3
CN CH N CH N t-Bu Cl CF.sub.3 CN CH CH CH CCl Et Me CF.sub.3 Cl CH
CH CH CCl i-Pr Me CF.sub.3 Cl CH CH CH CCl t-Bu Me CF.sub.3 Cl CH
CH CH CCl Et Me CF.sub.3 Br CH CH CH CCl i-Pr Me CF.sub.3 Br CH CH
CH CCl t-Bu Me CF.sub.3 Br CH CH CH CCl Et Me CF.sub.3 I CH CH CH
CCl i-Pr Me CF.sub.3 I CH CH CH CCl t-Bu Me CF.sub.3 I CH CH CH CCl
Et Me CF.sub.3 F CH CH CH CCl i-Pr Me CF.sub.3 F CH CH CH CCl t-Bu
Me CF.sub.3 F CH CH CH CCl Et Me CF.sub.3 Me CH CH CH CCl i-Pr Me
CF.sub.3 Me CH CH CH CCl t-Bu Me CF.sub.3 Me CH CH CH CCl Et Me
CF.sub.3 CF.sub.3 CH CH CH CCl i-Pr Me CF.sub.3 CF.sub.3 CH CH CH
CCl t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CCl Et Me CF.sub.3 OMe CH CH
CH CCl i-Pr Me CF.sub.3 OMe CH CH CH CCl t-Bu Me CF.sub.3 OMe CH CH
CH CCl Et Me CF.sub.3 CN CH CH CH CCl i-Pr Me CF.sub.3 CN CH CH CH
CCl t-Bu Me CF.sub.3 CN CH CH CH CCl Et Cl CF.sub.3 Cl CH CH CH CCl
i-Pr Cl CF.sub.3 Cl CH CH CH CCl t-Bu Cl CF.sub.3 Cl CH CH CH CCl
Et Cl CF.sub.3 Br CH CH CH CCl i-Pr Cl CF.sub.3 Br CH CH CH CCl
t-Bu Cl CF.sub.3 Br CH CH CH CCl Et Cl CF.sub.3 I CH CH CH CCl i-Pr
Cl CF.sub.3 I CH CH CH CCl t-Bu Cl CF.sub.3 I CH CH CH CCl Et Cl
CF.sub.3 F CH CH CH CCl i-Pr Cl CF.sub.3 F CH CH CH CCl t-Bu Cl
CF.sub.3 F CH CH CH CCl Et Cl CF.sub.3 Me CH CH CH CCl i-Pr Cl
CF.sub.3 Me CH CH CH CCl t-Bu Cl CF.sub.3 Me CH CH CH CCl Et Cl
CF.sub.3 CF.sub.3 CH CH CH CCl i-Pr Cl CF.sub.3 CF.sub.3 CH CH CH
CCl t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CCl Et Cl CF.sub.3 OMe CH CH
CH CCl i-Pr Cl CF.sub.3 OMe CH CH CH CCl t-Bu Cl CF.sub.3 OMe CH CH
CH CCl Et Cl CF.sub.3 CN CH CH CH CCl i-Pr Cl CF.sub.3 CN CH CH CH
CCl t-Bu Cl CF.sub.3 CN CH CH CH CF Et Me CF.sub.3 Cl CH CH CH CF
i-Pr Me CF.sub.3 Cl CH CH CH CF t-Bu Me CF.sub.3 Cl CH CH CH CF Et
Me CF.sub.3 Br CH CH CH CF i-Pr Me CF.sub.3 Br CH CH CH CF t-Bu Me
CF.sub.3 Br CH CH CH CF Et Me CF.sub.3 I CH CH CH CF i-Pr Me
CF.sub.3 I CH CH CH CF t-Bu Me CF.sub.3 I CH CH CH CF Et Me
CF.sub.3 F CH CH CH CF i-Pr Me CF.sub.3 F CH CH CH CF t-Bu Me
CF.sub.3 F CH CH CH CF Et Me CF.sub.3 Me CH CH CH CF i-Pr Me
CF.sub.3 Me CH CH CH CF t-Bu Me CF.sub.3 Me CH CH CH CF Et Me
CF.sub.3 CF.sub.3 CH CH CH CF i-Pr Me CF.sub.3 CF.sub.3 CH CH CH CF
t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CF Et Me CF.sub.3 OMe CH CH CH
CF i-Pr Me CF.sub.3 OMe CH CH CH CF t-Bu Me CF.sub.3 OMe CH CH CH
CF Et Me CF.sub.3 CN CH CH CH CF i-Pr Me CF.sub.3 CN CH CH CH CF
t-Bu Me CF.sub.3 CN CH CH CH CF Et Cl CF.sub.3 Cl CH CH CH CF i-Pr
Cl CF.sub.3 Cl CH CH CH CF t-Bu Cl CF.sub.3 Cl CH CH CH CF Et Cl
CF.sub.3 Br CH CH CH CF i-Pr Cl CF.sub.3 Br CH CH CH CF t-Bu Cl
CF.sub.3 Br CH CH CH CF Et Cl CF.sub.3 I CH CH CH CF i-Pr Cl
CF.sub.3 I CH CH CH CF t-Bu Cl CF.sub.3 I CH CH CH CF i-Pr Cl
CF.sub.3 F CH CH CH CF t-Bu Cl CF.sub.3 F CH CH CH CF Et Cl
CF.sub.3 Me CH CH CH CF i-Pr Cl CF.sub.3 Me CH CH CH CF t-Bu Cl
CF.sub.3 Me CH CH CH CF Et Cl CF.sub.3 CF.sub.3 CH CH CH CF i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH CF t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CF
Et Cl CF.sub.3 OMe CH CH CH CF i-Pr Cl CF.sub.3 OMe CH CH CH CF
t-Bu Cl CF.sub.3 OMe CH CH CH CF Et Cl CF.sub.3 CN CH CH CH CF i-Pr
Cl CF.sub.3 CN CH CH CH CF t-Bu Cl CF.sub.3 CN CH CH CH CH Et Me
C.sub.2F.sub.5 Cl CH CH CH CH i-Pr Me C.sub.2F.sub.5 Cl CH CH CH CH
t-Bu Me C.sub.2F.sub.5 Cl CH CH CH CH Et Me C.sub.2F.sub.5 Br CH CH
CH CH i-Pr Me C.sub.2F.sub.5 Br CH CH CH CH t-Bu Me C.sub.2F.sub.5
Br CH CH CH CH Et Me C.sub.2F.sub.5 I CH CH CH CH i-Pr Me
C.sub.2F.sub.5 I CH CH CH CH t-Bu Me C.sub.2F.sub.5 I CH CH CH CH
Et Me C.sub.2F.sub.5 F CH CH CH CH i-Pr Me C.sub.2F.sub.5 F CH CH
CH CH t-Bu Me C.sub.2F.sub.5 F CH CH CH CH Et Me C.sub.2F.sub.5 Me
CH CH CH CH i-Pr Me C.sub.2F.sub.5 Me CH CH CH CH t-Bu Me
C.sub.2F.sub.5 Me CH CH CH CH Et Me C.sub.2F.sub.5 CF.sub.3 CH CH
CH CH i-Pr Me C.sub.2F.sub.5 CF.sub.3 CH CH CH CH t-Bu Me
C.sub.2F.sub.5 CF.sub.3 CH CH CH CH Et Me C.sub.2F.sub.5 OMe CH CH
CH CH i-Pr Me C.sub.2F.sub.5 OMe CH CH CH CH t-Bu Me C.sub.2F.sub.5
OMe CH CH CH CH Et Me C.sub.2F.sub.5 CN CH CH CH CH i-Pr Me
C.sub.2F.sub.5 CN CH CH CH CH t-Bu Me C.sub.2F.sub.5 CN CH CH CH CH
Et Cl C.sub.2F.sub.5 Cl CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Cl CH CH
CH CH t-Bu Cl C.sub.2F.sub.5 Cl CH CH CH CH Et Cl C.sub.2F.sub.5 Br
CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Br CH CH CH CH t-Bu Cl
C.sub.2F.sub.5 Br CH CH CH CH Et Cl C.sub.2F.sub.5 I CH CH CH CH
i-Pr Cl C.sub.2F.sub.5 I CH CH CH CH t-Bu Cl C.sub.2F.sub.5 I CH CH
CH CH Et Cl C.sub.2F.sub.5 F CH CH CH CH i-Pr Cl C.sub.2F.sub.5 F
CH CH CH CH t-Bu Cl C.sub.2F.sub.5 F CH CH CH CH Et Cl
C.sub.2F.sub.5 Me CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Me CH CH CH CH
t-Bu Cl C.sub.2F.sub.5 Me CH CH CH CH Et Cl C.sub.2F.sub.5 CF.sub.3
CH CH CH CH i-Pr Cl C.sub.2F.sub.5 CF.sub.3 CH CH CH CH t-Bu Cl
C.sub.2F.sub.5 CF.sub.3 CH CH CH CH Et Cl C.sub.2F.sub.5 OMe CH CH
CH CH i-Pr Cl C.sub.2F.sub.5 OMe CH CH CH CH t-Bu Cl C.sub.2F.sub.5
OMe CH CH CH CH Et Cl C.sub.2F.sub.5 CN CH CH CH CH i-Pr Cl
C.sub.2F.sub.5 CN CH CH CH CH t-Bu Cl C.sub.2F.sub.5 CN
[0353]
17TABLE 17 56 W X Y Z R.sup.3 R.sup.4 R.sup.7 R.sup.8 CH CH CH CH
Et Me CF.sub.3 Cl CH CH CH CH i-Pr Me CF.sub.3 Cl CH CH CH CH t-Bu
Me CF.sub.3 Cl CH CH CH CH Et Me CF.sub.3 Br CH CH CH CH i-Pr Me
CF.sub.3 Br CH CH CH CH t-Bu Me CF.sub.3 Br CH CH CH CH Et Me
CF.sub.3 I CH CH CH CH i-Pr Me CF.sub.3 I CH CH CH CH t-Bu Me
CF.sub.3 I CH CH CH CH Et Me CF.sub.3 F CH CH CH CH i-Pr Me
CF.sub.3 F CH CH CH CH t-Bu Me CF.sub.3 F CH CH CH CH Et Me
CF.sub.3 Me CH CH CH CH i-Pr Me CF.sub.3 Me CH CH CH CH t-Bu Me
CF.sub.3 Me CH CH CH CH Et Me CF.sub.3 CF.sub.3 CH CH CH CH i-Pr Me
CF.sub.3 CF.sub.3 CH CH CH CH t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CH
Et Me CF.sub.3 OMe CH CH CH CH i-Pr Me CF.sub.3 OMe CH CH CH CH
t-Bu Me CF.sub.3 OMe CH CH CH CH Et Me CF.sub.3 CN CH CH CH CH i-Pr
Me CF.sub.3 CN CH CH CH CH t-Bu Me CF.sub.3 CN CH CH CH CH Et Cl
CF.sub.3 Cl CH CH CH CH i-Pr Cl CF.sub.3 Cl CH CH CH CH t-Bu Cl
CF.sub.3 Cl CH CH CH CH Et Cl CF.sub.3 Br CH CH CH CH i-Pr Cl
CF.sub.3 Br CH CH CH CH t-Bu Cl CF.sub.3 Br CH CH CH CH Et Cl
CF.sub.3 I CH CH CH CH i-Pr Cl CF.sub.3 I CH CH CH CH t-Bu Cl
CF.sub.3 I CH CH CH CH Et Cl CF.sub.3 F CH CH CH CH i-Pr Cl
CF.sub.3 F CH CH CH CH t-Bu Cl CF.sub.3 F CH CH CH CH Et Cl
CF.sub.3 Me CH CH CH CH i-Pr Cl CF.sub.3 Me CH CH CH CH t-Bu Cl
CF.sub.3 Me CH CH CH CH Et Cl CF.sub.3 CF.sub.3 CH CH CH CH i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH CH t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CH
Et Cl CF.sub.3 OMe CH CH CH CH i-Pr Cl CF.sub.3 OMe CH CH CH CH
t-Bu Cl CF.sub.3 OMe CH CH CH CH Et Cl CF.sub.3 CN CH CH CH CH i-Pr
Cl CF.sub.3 CN CH CH CH CH t-Bu Cl CF.sub.3 CN CH CH CH N Et Me
CF.sub.3 Cl CH CH CH N i-Pr Me CF.sub.3 Cl CH CH CH N t-Bu Me
CF.sub.3 Cl CH CH CH N Et Me CF.sub.3 Br CH CH CH N i-Pr Me
CF.sub.3 Br CH CH CH N t-Bu Me CF.sub.3 Br CH CH CH N Et Me
CF.sub.3 I CH CH CH N i-Pr Me CF.sub.3 I CH CH CH N t-Bu Me
CF.sub.3 I CH CH CH N Et Me CF.sub.3 F CH CH CH N i-Pr Me CF.sub.3
F CH CH CH N t-Bu Me CF.sub.3 F CH CH CH N Et Me CF.sub.3 Me CH CH
CH N i-Pr Me CF.sub.3 Me CH CH CH N t-Bu Me CF.sub.3 Me CH CH CH N
Et Me CF.sub.3 CF.sub.3 CH CH CH N i-Pr Me CF.sub.3 CF.sub.3 CH CH
CH N t-Bu Me CF.sub.3 CF.sub.3 CH CH CH N Et Me CF.sub.3 OMe CH CH
CH N i-Pr Me CF.sub.3 OMe CH CH CH N t-Bu Me CF.sub.3 OMe CH CH CH
N Et Me CF.sub.3 CN CH CH CH N i-Pr Me CF.sub.3 CN CH CH CH N t-Bu
Me CF.sub.3 CN CH CH CH N Et Cl CF.sub.3 Cl CH CH CH N i-Pr Cl
CF.sub.3 Cl CH CH CH N t-Bu Cl CF.sub.3 Cl CH CH CH N Et Cl
CF.sub.3 Br CH CH CH N i-Pr Cl CF.sub.3 Br CH CH CH N t-Bu Cl
CF.sub.3 Br CH CH CH N Et Cl CF.sub.3 I CH CH CH N i-Pr Cl CF.sub.3
I CH CH CH N t-Bu Cl CF.sub.3 I CH CH CH N Et Cl CF.sub.3 F CH CH
CH N i-Pr Cl CF.sub.3 F CH CH CH N t-Bu Cl CF.sub.3 F CH CH CH N Et
Cl CF.sub.3 Me CH CH CH N i-Pr Cl CF.sub.3 Me CH CH CH N t-Bu Cl
CF.sub.3 Me CH CH CH N Et Cl CF.sub.3 CF.sub.3 CH CH CH N i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH N t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH N
Et Cl CF.sub.3 OMe CH CH CH N i-Pr Cl CF.sub.3 OMe CH CH CH N t-Bu
Cl CF.sub.3 OMe CH CH CH N Et Cl CF.sub.3 CN CH CH CH N i-Pr Cl
CF.sub.3 CN CH CH CH N t-Bu Cl CF.sub.3 CN CH CH N CH Et Me
CF.sub.3 Cl CH CH N CH i-Pr Me CF.sub.3 Cl CH CH N CH t-Bu Me
CF.sub.3 Cl CH CH N CH Et Me CF.sub.3 Br CH CH N CH i-Pr Me
CF.sub.3 Br CH CH N CH t-Bu Me CF.sub.3 Br CH CH N CH Et Me
CF.sub.3 I CH CH N CH i-Pr Me CF.sub.3 I CH CH N CH t-Bu Me
CF.sub.3 I CH CH N CH Et Me CF.sub.3 F CH CH N CH i-Pr Me CF.sub.3
F CH CH N CH t-Bu Me CF.sub.3 F CH CH N CH Et Me CF.sub.3 Me CH CH
N CH i-Pr Me CF.sub.3 Me CH CH N CH t-Bu Me CF.sub.3 Me CH CH N CH
Et Me CF.sub.3 CF.sub.3 CH CH N CH i-Pr Me CF.sub.3 CF.sub.3 CH CH
N CH t-Bu Me CF.sub.3 CF.sub.3 CH CH N CH Et Me CF.sub.3 OMe CH CH
N CH i-Pr Me CF.sub.3 OMe CH CH N CH t-Bu Me CF.sub.3 OMe CH CH N
CH Et Me CF.sub.3 CN CH CH N CH i-Pr Me CF.sub.3 CN CH CH N CH t-Bu
Me CF.sub.3 CN CH CH N CH Et Cl CF.sub.3 Cl CH CH N CH i-Pr Cl
CF.sub.3 Cl CH CH N CH t-Bu Cl CF.sub.3 Cl CH CH N CH Et Cl
CF.sub.3 Br CH CH N CH i-Pr Cl CF.sub.3 Br CH CH N CH t-Bu Cl
CF.sub.3 Br CH CH N CH Et Cl CF.sub.3 I CH CH N CH i-Pr Cl CF.sub.3
I CH CH N CH t-Bu Cl CF.sub.3 I CH CH N CH Et Cl CF.sub.3 F CH CH N
CH i-Pr Cl CF.sub.3 F CH CH N CH t-Bu Cl CF.sub.3 F CH CH N CH Et
Cl CF.sub.3 Me CH CH N CH i-Pr Cl CF.sub.3 Me CH CH N CH t-Bu Cl
CF.sub.3 Me CH CH N CH Et Cl CF.sub.3 CF.sub.3 CH CH N CH i-Pr Cl
CF.sub.3 CF.sub.3 CH CH N CH t-Bu Cl CF.sub.3 CF.sub.3 CH CH N CH
Et Cl CF.sub.3 OMe CH CH N CH i-Pr Cl CF.sub.3 OMe CH CH N CH t-Bu
Cl CF.sub.3 OMe CH CH N CH Et Cl CF.sub.3 CN CH CH N CH i-Pr Cl
CF.sub.3 CN CH CH N CH t-Bu Cl CF.sub.3 CN CH N CH CH Et Me
CF.sub.3 Cl CH N CH CH i-Pr Me CF.sub.3 Cl CH N CH CH t-Bu Me
CF.sub.3 Cl CH N CH CH Et Me CF.sub.3 Br CH N CH CH i-Pr Me
CF.sub.3 Br CH N CH CH t-Bu Me CF.sub.3 Br CH N CH CH Et Me
CF.sub.3 I CH N CH CH i-Pr Me CF.sub.3 I CH N CH CH t-Bu Me
CF.sub.3 I CH N CH CH Et Me CF.sub.3 F CH N CH CH i-Pr Me CF.sub.3
F CH N CH CH t-Bu Me CF.sub.3 F CH N CH CH Et Me CF.sub.3 Me CH N
CH CH i-Pr Me CF.sub.3 Me CH N CH CH t-Bu Me CF.sub.3 Me CH N CH CH
Et Me CF.sub.3 CF.sub.3 CH N CH CH i-Pr Me CF.sub.3 CF.sub.3 CH N
CH CH t-Bu Me CF.sub.3 CF.sub.3 CH N CH CH Et Me CF.sub.3 OMe CH N
CH CH i-Pr Me CF.sub.3 OMe CH N CH CH t-Bu Me CF.sub.3 OMe CH N CH
CH Et Me CF.sub.3 CN CH N CH CH i-Pr Me CF.sub.3 CN CH N CH CH t-Bu
Me CF.sub.3 CN CH N CH CH Et Cl CF.sub.3 Cl CH N CH CH i-Pr Cl
CF.sub.3 Cl CH N CH CH t-Bu Cl CF.sub.3 Cl CH N CH CH Et Cl
CF.sub.3 Br CH N CH CH i-Pr Cl CF.sub.3 Br CH N CH CH t-Bu Cl
CF.sub.3 Br CH N CH CH Et Cl CF.sub.3 I CH N CH CH i-Pr Cl CF.sub.3
I CH N CH CH t-Bu Cl CF.sub.3 I CH N CH CH Et Cl CF.sub.3 F CH N CH
CH i-Pr Cl CF.sub.3 F CH N CH CH t-Bu Cl CF.sub.3 F CH N CH CH Et
Cl CF.sub.3 Me CH N CH CH i-Pr Cl CF.sub.3 Me CH N CH CH t-Bu Cl
CF.sub.3 Me CH N CH CH Et Cl CF.sub.3 CF.sub.3 CH N CH CH i-Pr Cl
CF.sub.3 CF.sub.3 CH N CH CH t-Bu Cl CF.sub.3 CF.sub.3 CH N CH CH
Et Cl CF.sub.3 OMe CH N CH CH i-Pr Cl CF.sub.3 OMe CH N CH CH t-Bu
Cl CF.sub.3 OMe CH N CH CH Et Cl CF.sub.3 CN CH N CH CH i-Pr Cl
CF.sub.3 CN CH N CH CH t-Bu Cl CF.sub.3 CN N CH CH CH Et Me
CF.sub.3 Cl N CH CH CH i-Pr Me CF.sub.3 Cl N CH CH CH t-Bu Me
CF.sub.3 Cl N CH CH CH Et Me CF.sub.3 Br N CH CH CH i-Pr Me
CF.sub.3 Br N CH CH CH t-Bu Me CF.sub.3 Br N CH CH CH Et Me
CF.sub.3 I N CH CH CH i-Pr Me CF.sub.3 I N CH CH CH t-Bu Me
CF.sub.3 I N CH CH CH Et Me CF.sub.3 F N CH CH CH i-Pr Me CF.sub.3
F N CH CH CH t-Bu Me CF.sub.3 F N CH CH CH Et Me CF.sub.3 Me N CH
CH CH i-Pr Me CF.sub.3 Me N CH CH CH t-Bu Me CF.sub.3 Me N CH CH CH
Et Me CF.sub.3 CF.sub.3 N CH CH CH i-Pr Me CF.sub.3 CF.sub.3 N CH
Cu CH t-Bu Me CF.sub.3 CF.sub.3 N CH CH CH Et Me CF.sub.3 OMe N CH
CH CH i-Pr Me CF.sub.3 OMe N CH CH CH t-Bu Me CF.sub.3 OMe N CH CH
CH Et Me CF.sub.3 CN N CH CH CH i-Pr Me CF.sub.3 CN N CH CH CH t-Bu
Me CF.sub.3 CN N CH CH CH Et Cl CF.sub.3 Cl N CH CH CH i-Pr Cl
CF.sub.3 Cl N CH CH CH t-Bu Cl CF.sub.3 Cl N CH CH CH Et Cl
CF.sub.3 Br N CH CH CH i-Pr Cl CF.sub.3 Br N CH CH CH t-Bu Cl
CF.sub.3 Br N CH CH CH Et Cl CF.sub.3 I N CH CH CH i-Pr Cl CF.sub.3
I N CH CH CH t-Bu Cl CF.sub.3 I N CH CH CH Et Cl CF.sub.3 F N CH CH
CH i-Pr Cl CF.sub.3 F N CH CH CH t-Bu Cl CF.sub.3 F N CH CH CH Et
Cl CF.sub.3 Me N CH CH CH i-Pr Cl CF.sub.3 Me N CH CH CH t-Bu Cl
CF.sub.3 Me N CH CH CH Et Cl CF.sub.3 CF.sub.3 N CH CH CH i-Pr Cl
CF.sub.3 CF.sub.3 N CH CH CH t-Bu Cl CF.sub.3 CF.sub.3 N CH CH CH
Et Cl CF.sub.3 OMe N CH CH CH i-Pr Cl CF.sub.3 OMe N CH CH CH t-Bu
Cl CF.sub.3 OMe N CH CH CH Et Cl CF.sub.3 CN N CH CH CH i-Pr Cl
CF.sub.3 CN N CH CH CH t-Bu Cl CF.sub.3 CN CH N CH N Et Me CF.sub.3
Cl CH N CH N i-Pr Me CF.sub.3 Cl CH N CH N t-Bu Me CF.sub.3 Cl CH N
CH N Et Me CF.sub.3 Br CH N CH N i-Pr Me CF.sub.3 Br CH N CH N t-Bu
Me CF.sub.3 Br CH N CH N Et Me CF.sub.3 I CH N CH N i-Pr Me
CF.sub.3 I CH N CH N t-Bu Me CF.sub.3 I CH N CH N Et Me CF.sub.3 F
CH N CH N i-Pr Me CF.sub.3 F CH N CH N t-Bu Me CF.sub.3 F CH N CH N
Et Me CF.sub.3 Me CH N CH N i-Pr Me CF.sub.3 Me CH N CH N t-Bu Me
CF.sub.3 Me CH N CH N Et Me CF.sub.3 CF.sub.3 CH N CH N i-Pr Me
CF.sub.3 CF.sub.3 CH N CH N t-Bu Me CF.sub.3 CF.sub.3 CH N CH N Et
Me CF.sub.3 OMe CH N CH N i-Pr Me CF.sub.3 OMe CH N CH N t-Bu Me
CF.sub.3 OMe CH N CH N Et Me CF.sub.3 CN CH N CH N i-Pr Me CF.sub.3
CN CH N CH N t-Bu Me CF.sub.3 CN CH N CH N Et Cl CF.sub.3 Cl CH N
CH N i-Pr Cl CF.sub.3 Cl CH N CH N t-Bu Cl CF.sub.3 Cl CH N CH N Et
Cl CF.sub.3 Br CH N CH N i-Pr Cl CF.sub.3 Br CH N CH N t-Bu Cl
CF.sub.3 Br CH N CH N Et Cl CF.sub.3 I CH N CH N i-Pr Cl CF.sub.3 I
CH N CH N t-Bu Cl CF.sub.3 I CH N CH N Et Cl CF.sub.3 F CH N CH N
i-Pr Cl CF.sub.3 F CH N CH N t-Bu Cl CF.sub.3 F CH N CH N Et Cl
CF.sub.3 Me CH N CH N i-Pr Cl CF.sub.3 Me CH N CH N t-Bu Cl
CF.sub.3 Me CH N CH N Et Cl CF.sub.3 CF.sub.3 CH N CH N i-Pr Cl
CF.sub.3 CF.sub.3 CH N CH N t-Bu Cl CF.sub.3 CF.sub.3 CH N CH N Et
Cl CF.sub.3 OMe CH N CH N i-Pr Cl CF.sub.3 OMe CH N CH N t-Bu Cl
CF.sub.3 OMe CH N CH N Et Cl CF.sub.3 CN CH N CH N i-Pr Cl CF.sub.3
CN CH N CH N t-Bu Cl CF.sub.3 CN CH CH CH CCl Et Me CF.sub.3 Cl CH
CH CH CCl i-Pr Me CF.sub.3 Cl CH CH CH CCl t-Bu Me CF.sub.3 Cl CH
CH CH CCl Et Me CF.sub.3 Br CH CH CH CCl i-Pr Me CF.sub.3 Br CH CH
CH CCl t-Bu Me CF.sub.3 Br CH CH CH CCl Et Me CF.sub.3 I CH CH CH
CCl i-Pr Me CF.sub.3 I CH CH CH CCl t-Bu Me CF.sub.3 I CH CH CH CCl
Et Me CF.sub.3 F CH CH CH CCl i-Pr Me CF.sub.3 F CH CH CH CCl t-Bu
Me CF.sub.3 F CH CH CH CCl Et Me CF.sub.3 Me CH CH CH CCl i-Pr Me
CF.sub.3 Me CH CH CH CCl t-Bu Me CF.sub.3 Me CH CH CH CCl Et Me
CF.sub.3 CF.sub.3 CH CH CH CCl i-Pr Me CF.sub.3 CF.sub.3 CH CH CH
CCl t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CCl Et Me CF.sub.3 OMe CH CH
CH CCl i-Pr Me CF.sub.3 OMe CH CH CH CCl t-Bu Me CF.sub.3 OMe CH CH
CH CCl Et Me CF.sub.3 CN CH CH CH CCl i-Pr Me CF.sub.3 CN CH CH CH
CCl t-Bu Me CF.sub.3 CN CH CH CH CCl Et Cl CF.sub.3 Cl CH CH CH CCl
i-Pr Cl CF.sub.3 Cl CH CH CH CCl t-Bu Cl CF.sub.3 Cl CH CH CH CCl
Et Cl CF.sub.3 Br CH CH CH CCl i-Pr Cl CF.sub.3 Br CH CH CH CCl
t-Bu Cl CF.sub.3 Br CH CH CH CCl Et Cl CF.sub.3 I CH CH CH CCl i-Pr
Cl CF.sub.3 I CH CH CH CCl t-Bu Cl CF.sub.3 I CH CH CH CCl Et Cl
CF.sub.3 F CH CH CH CCl i-Pr Cl CF.sub.3 F CH CH CH CCl t-Bu Cl
CF.sub.3 F CH CH CH CCl Et Cl CF.sub.3 Me CH CH CH CCl i-Pr Cl
CF.sub.3 Me CH CH CH CCl t-Bu Cl CF.sub.3 Me CH CH CH CCl Et Cl
CF.sub.3 CF.sub.3 CH CH CH CCl i-Pr Cl CF.sub.3 CF.sub.3 CH CH CH
CCl t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CCl Et Cl CF.sub.3 OMe CH CH
CH CCl i-Pr Cl CF.sub.3 OMe CH CH CH CCl t-Bu Cl CF.sub.3 OMe CH CH
CH CCl Et Cl CF.sub.3 CN CH CH CH CCl i-Pr Cl CF.sub.3 CN CH CH CH
CCl t-Bu Cl CF.sub.3 CN CH CH CH CF Et Me CF.sub.3 Cl CH CH CH CF
i-Pr Me CF.sub.3 Cl CH CH CH CF t-Bu Me CF.sub.3 Cl CH CH CH CF Et
Me CF.sub.3 Br CH CH CH CF i-Pr Me CF.sub.3 Br CH CH CH CF t-Bu Me
CF.sub.3 Br CH CH CH CF Et Me CF.sub.3 I CH CH CH CF i-Pr Me
CF.sub.3 I CH CH CH CF t-Bu Me CF.sub.3 I CH CH CH CF Et Me
CF.sub.3 F CH CH CH CF i-Pr Me CF.sub.3 F CH CH CH CF t-Bu Me
CF.sub.3 F CH CH CH CF Et Me CF.sub.3 Me CH CH CH CF i-Pr Me
CF.sub.3 Me CH CH CH CF t-Bu Me CF.sub.3 Me CH CH CH CF Et Me
CF.sub.3 CF.sub.3 CH CH CH CF i-Pr Me CF.sub.3 CF.sub.3 CH CH CH CF
t-Bu Me CF.sub.3 CF.sub.3 CH CH CH CF Et Me CF.sub.3 OMe CH CH CH
CF i-Pr Me CF.sub.3 OMe CH CH CH CF t-Bu Me CF.sub.3 OMe CH CH CH
CF Et Me CF.sub.3 CN CH CH CH CF i-Pr Me CF.sub.3 CN CH CH CH CF
t-Bu Me CF.sub.3 CN CH CH CH CF Et Cl CF.sub.3 Cl CH CH CH CF i-Pr
Cl CF.sub.3 Cl CH CH CH CF t-Bu Cl CF.sub.3 Cl CH CH CH CF Et Cl
CF.sub.3 Br CH CH CH CF i-Pr Cl CF.sub.3 Br CH CH CH CF t-Bu Cl
CF.sub.3 Br CH CH CH CF Et Cl CF.sub.3 I CH CH CH CF i-Pr Cl
CF.sub.3 I CH CH CH CF t-Bu Cl CF.sub.3 I CH CH CH CF i-Pr Cl
CF.sub.3 F CH CH CH CF t-Bu Cl CF.sub.3 F CH CH CH CF Et Cl
CF.sub.3 Me CH CH CH CF i-Pr Cl CF.sub.3 Me CH CH CH CF t-Bu Cl
CF.sub.3 Me CH CH CH CF Et Cl CF.sub.3 CF.sub.3 CH CH CH CF i-Pr Cl
CF.sub.3 CF.sub.3 CH CH CH CF t-Bu Cl CF.sub.3 CF.sub.3 CH CH CH CF
Et Cl CF.sub.3 OMe CH CH CH CF i-Pr Cl CF.sub.3 OMe CH CH CH CF
t-Bu Cl CF.sub.3 OMe CH CH CH CF Et Cl CF.sub.3 CN CH CH CH CF i-Pr
Cl CF.sub.3 CN CH CH CH CF t-Bu Cl CF.sub.3 CN CH CH CH CH Et Me
C.sub.2F.sub.5 Cl CH CH CH CH i-Pr Me C.sub.2F.sub.5 Cl CH CH CH CH
t-Bu Me C.sub.2F.sub.5 Cl CH CH CH CH Et Me C.sub.2F.sub.5 Br CH CH
CH CH i-Pr Me C.sub.2F.sub.5 Br CH CH CH CH t-Bu Me C.sub.2F.sub.5
Br CH CH CH CH Et Me C.sub.2F.sub.5 I CH CH CH CH i-Pr Me
C.sub.2F.sub.5 I CH CH CH CH t-Bu Me C.sub.2F.sub.5 I CH CH CH CH
Et Me C.sub.2F.sub.5 F CH CH CH CH i-Pr Me C.sub.2F.sub.5 F CH CH
CH CH t-Bu Me C.sub.2F.sub.5 F CH CH CH CH Et Me C.sub.2F.sub.5 Me
CH CH CH CH i-Pr Me C.sub.2F.sub.5 Me CH CH CH CH t-Bu Me
C.sub.2F.sub.5 Me CH CH CH CH Et Me C.sub.2F.sub.5 CF.sub.3 CH CH
CH CH i-Pr Me C.sub.2F.sub.5 CF.sub.3 CH CH CH CH t-Bu Me
C.sub.2F.sub.5 CF.sub.3 CH CH CH CH Et Me C.sub.2F.sub.5 OMe CH CH
CH CH i-Pr Me C.sub.2F.sub.5 OMe CH CH CH CH t-Bu Me C.sub.2F.sub.5
OMe CH CH CH CH Et Me C.sub.2F.sub.5 CN CH CH CH CH i-Pr Me
C.sub.2F.sub.5 CN CH CH CH CH t-Bu Me C.sub.2F.sub.5 CN CH CH CH CH
Et Cl C.sub.2F.sub.5 Cl CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Cl CH CH
CH CH t-Bu Cl C.sub.2F.sub.5 Cl CH CH CH CH Et Cl C.sub.2F.sub.5 Br
CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Br CH CH CH CH t-Bu Cl
C.sub.2F.sub.5 Br CH CH CH CH Et Cl C.sub.2F.sub.5 I CH CH CH CH
i-Pr Cl C.sub.2F.sub.5 I CH CH CH CH t-Bu Cl C.sub.2F.sub.5 I CH CH
CH CH Et Cl C.sub.2F.sub.5 F CH CH CH CH i-Pr Cl C.sub.2F.sub.5 F
CH CH CH CH t-Bu Cl C.sub.2F.sub.5 F CH CH CH CH Et Cl
C.sub.2F.sub.5 Me CH CH CH CH i-Pr Cl C.sub.2F.sub.5 Me CH CH CH CH
t-Bu Cl C.sub.2F.sub.5 Me CH CH CH CH Et Cl C.sub.2F.sub.5 CF.sub.3
CH CH CH CH i-Pr Cl C.sub.2F.sub.5 CF.sub.3 CH CH CH CH t-Bu Cl
C.sub.2F.sub.5 CF.sub.3 CH CH CH CH Et Cl C.sub.2F.sub.5 OMe CH CH
CH CH i-Pr Cl C.sub.2F.sub.5 OMe CH CH CH CH t-Bu Cl C.sub.2F.sub.5
OMe CH CH CH CH Et Cl C.sub.2F.sub.5 CN CH CH CH CH i-Pr Cl
C.sub.2F.sub.5 CN CH CH CH CH t-Bu Cl C.sub.2F.sub.5 CN
[0354] Formulation/Utility
[0355] Compounds of this invention will generally be used as a
formulation or composition with an agriculturally suitable carrier
comprising at least one of a liquid diluent, a solid diluent or a
surfactant. The formulation or composition ingredients are selected
to be consistent with the physical properties of the active
ingredient, mode of application and environmental factors such as
soil type, moisture and temperature. Useful formulations include
liquids such as solutions (including emulsifiable concentrates),
suspensions, emulsions (including microemulsions and/or
suspoemulsions) and the like which optionally can be thickened into
gels. Useful formulations further include solids such as dusts,
powders, granules, pellets, tablets, films, and the like which can
be water-dispersible ("wettable") or water-soluble. Active
ingredient can be (micro)encapsulated and further formed into a
suspension or solid formulation; alternatively the entire
formulation of active ingredient can be encapsulated (or
"overcoated"). Encapsulation can control or delay release of the
active ingredient. Sprayable formulations can be extended in
suitable media and used at spray volumes from about one to several
hundred liters per hectare. High-strength compositions are
primarily used as intermediates for further formulation.
[0356] The formulations will typically-contain effective amounts of
active ingredient, diluent and surfactant within the following
approximate ranges that add up to 100 percent by weight.
18 Weight Percent Active Ingredient Diluent Surfactant
Water-Dispersible and Water- 5-90 0-94 1-15 soluble Granules,
Tablets and Powders. Suspensions, Emulsions, 5-50 40-95 0-15
Solutions (including Emulsifiable Concentrates) Dusts 1-25 70-99
0-5 Granules and Pellets 0.01-99 5-99.99 0-15 High Strength
Compositions 90-99 0-10 0-2
[0357] Typical solid diluents are described in Watkins, et al.,
Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed.,
Dorland Books, Caldwell, N.J. Typical liquid diluents are described
in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.
McCutcheon's Detergents and Emulsifiers Annual, Allured Publ.
Corp., Ridgewood, N.J., as well as Sisely and Wood, Encyclopedia of
Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964,
list surfactants and recommended uses. All formulations can contain
minor amounts of additives to reduce foam, caking, corrosion,
microbiological growth and the like, or thickeners to increase
viscosity.
[0358] Surfactants include, for example, polyethoxylated alcohols,
polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid
esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene
sulfonates, organosilicones, N,N-dialkyltaurates, lignin
sulfonates, naphthalene sulfonate formaldehyde condensates,
polycarboxylates, and polyoxyethylene/polyoxypropylene block
copolymers. Solid diluents include, for example, clays such as
bentonite, montmoriflonite, attapulgite and kaolin, starch, sugar,
silica, talc, diatomaceous earth, urea, calcium carbonate, sodium
carbonate and bicarbonate, and sodium sulfate. Liquid diluents
include, for example, water, N,N-dimethylformamide, dimethyl
sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene
glycol, paraffins, alkylbenzenes, alkcylnaphthalenes, oils of
olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed,
soybean, rape-seed and coconut, fatty acid esters, ketones such as
cyclohexanone, 2-heptanone, isophorone and
4-hydroxy-4methyl-2-pentanone, and alcohols such as methanol,
cyclohexanol, decanol and tetrahydrofurfuryl alcohol.
[0359] Solutions, including emulsifiable concentrates, can be
prepared by simply mixing the ingredients. Dusts and powders can be
prepared by blending and, usually, grinding as in a hammer mill or
fluid-energy mill. Suspensions are usually prepared by wet-milling;
see, for example, U.S. Pat. No. 3,060,084. Granules and pellets can
be prepared by spraying the active material upon preformed granular
carriers or by agglomeration techniques. See Browning,
"Agglomeration", Chemical Engineering, Dec. 4, 1967, pp 147-48,
Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New
York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can
be prepared as described in U.S. Pat. No. 4,172,714.
Water-dispersible and water-soluble granules can be prepared as
taught in U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442 and DE
3,246,493. Tablets can be prepared as taught in U.S. Pat No.
5,180,587, U.S. Pat. No. 5,232,701 and U.S. Pat. No. 5,208,030.
Films can be prepared as taught in GB 2,095,558 and U.S. Pat. No.
3,299,566.
[0360] For further information regarding the art of formulation,
see U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line
19 and Examples 1041; U.S. Pat. No. 3,309,192, Col. 5, line 43
through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,
132, 138-140, 162-164, 166, 167 and 169-182; U.S. Pat No.
2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples
1-4; Klingman, Weed Control as a Science, John Wiley and Sons,
Inc., New York, 1961, pp 81-96; and Hance et al., Weed Control
Handbook, 8th Ed., Blackwell Scientific Publications, Oxford,
1989.
[0361] In the following Examples, all percentages are by weight and
all formulations are prepared in conventional ways. Compound
numbers refer to compounds in Index Tables A.
19 Example A Wettable Powder Compound 1 65.0% dodecylphenol
polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium
silicoaluminate 6.0% montmorillonite (calcined) 23.0%. Example B
Granule Compound 1 10.0% attapulgite granules (low volatile matter,
90.0%. 0.71/0.30 mm; U.S.S. No. 25-50 sieves) Example C Extruded
Pellet Compound 1 25.0% anhydrous sodium sulfate 10.0% crude
calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0%
calcium/magnesium bentonite 59.0%. Example D Emulsifiable
Concentrate Compound 1 20.0% blend of oil soluble sulfonates 10.0%
and polyoxyethylene ethers isophorone 70.0%.
[0362] The compounds of this invention exhibit activity against a
wide spectrum of foliar-feeding, fruit-feeding, stem or root
feeding, seed-feeding, aquatic and soil-inhabiting arthropods (term
"arthropods" includes insects, mites and nematodes) which are pests
of growing and stored agronomic crops, forestry, greenhouse crops,
ornamentals, nursery crops, stored food and fiber products,
livestock, household, and public and animal health. Those skilled
in the art will appreciate that not all compounds are equally
effective against all growth stages of all pests. Nevertheless, all
of the compounds of this invention display activity against pests
that include: eggs, larvae and adults of the Order Lepidoptera;
eggs, foliar-feeding, fruit-feeding, root-feeding, seed-feeding
larvae and adults of the Order Coleoptera; eggs, immatures and
adults of the Orders Hemiptera and Homoptera; eggs, larvae, nymphs
and adults of the Order Acari; eggs, immatures and adults of the
Orders Thysanoptera, Orthoptera and Dermaptera; eggs, immatures and
adults of the Order Diptera; and eggs, juveniles and adults of the
Phylum Nematoda. The compounds of this invention are also active
against pests of the Orders Hymenoptera, Isoptera, Siphonaptera,
Blattaria, Thysanura and Psocoptera; pests belonging to the Class
Arachnida and Phylum Platyhelminthes. Specifically, the compounds
are active against southern corn rootworm (Diabrotica
undecimpunctata howardi), aster lealhopper (Mascrosteles
fascifrons), boll weevil (Anthonomus grandis), two-spotted spider
mite (Tetranychus urticae), fall armyworm (Spodoptera frugiperda),
black bean aphid (Aphis fabae), green peach aphid (Myzus persica),
cotton aphid (Aphis gossypii), Russian wheat aphid (Diuraphis
noxia), English grain aphid (Sitobion avenae), whitefly (Bemisia
tabacii), tobacco budworm (Heliothis virescens), rice water weevil
(Lissorhoptrus oryzophilus), rice leaf beetle (Oulema oryzae),
whitebacked planthopper (Sogatella furcifera), green leafhopper
(Nephotettix cincticeps), brown planthopper (Nilaparvata lugens),
small brown planthopper (Laodelphax striatellus), rice stem borer
(Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis),
black rice stink bug (Scotinophara lurida), rice stink bug (Oebalus
pugnax), rice bug (Leptocorisa chinensis), slender rice bug (Cletus
puntiger), southern green stink bug (Nezara viridula) and german
cockroach (Blatella germanica). The compounds are active on mites,
demonstrating ovicidal, larvicidal and chemosterilant activity
against such families as Tetranychidae including Tetranychus
urticae, Tetranychus cinnabarinus, Tetranychus mcdanieli,
Tetranychus pacificus, Tetranychus turkestani, Byrobia rubrioculus,
Panonychus ulmi, Panonychus citri, Eotetranychus carpini borealis,
Eotetranychus, hicoriae, Eotetranychus sexmaculatus,
Eotetranychusyumensis, Eotetranychus banksi and Oligonychus
pratensis; Tenuipalpidae including Brevipalpus lewisi,
Brevipalpusphoenicis, Brevipalpus californicus and Brevipalpus
obovatus; Eriophyidae including Phyllocoptruta oleivora, Eriophyes
sheldoni, Aculus cornutus, Epitrimerus pyri and Eriophyes
mangiferae. See WO 90/10623 and WO 92/00673 for more detailed pest
descriptions.
[0363] Compounds of this invention can also be mixed with one or
more other insecticides, fungicides, nematocides, bactericides,
acaricides, growth regulators, chemosterilants, semiochemicals,
repellents, attractants, pheromones, feeding stimulants or other
biologically active compounds to form a multi-component pesticide
giving an even broader spectrum of agricultural protection.
Examples of such agricultural protectants with which compounds of
this invention can be formulated are: insecticides such as
abamectin, acephate, avermectin, azinphos-methyl, bifenthrin,
buprofezin, carbofuran, chlorfenapyr, chlorpyrifos,
chlorpyrifos-methyl, clothianidin, cyfluthrin, beta-cyfluthrin,
cyhalothrin, lambda-cyhalothrin, cypermethrin, deltamethrin,
diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan,
emamectin, endosulfan, esfenvalerate, fenothicarb, fenoxycarb,
fenpropathrin, fenvalerate, fipronil, flucythrinate,
tau-fluvalinate, flufenoxuron, fonophos, imidacloprid, isofenphos,
malathion, metaldehyde, methamidophos, methidathion, methomyl,
methonrene, methoxychlor, methyl
7-chloro-2,5-dihydro-2-[[N-(methoxycarbonyl)-N-[4-(trifluoromethoxy)pheny-
lamino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylate
(indoxacarb), monocrotophos, oxamyl, parathion, parathion-methyl,
permetbrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb,
profenofos, pymetrozine, pyriproxyphen, rotenone, spionsad,
suiprofos, tebufenozide, tefluthrin, terbufos, tetrachlorvinphos,
thiacloprid, thiodicarb, tralomethrin, trichlorfon and triflumuron;
fungicides such as acibenzolar, azoxystrobin, benomyl,
blasticidin-S, Bordeaux mixture (Tribasic copper sulfate),
bromuconazole, carpropamid (KTU 3616), captafol, captan,
carbendazim, chloroneb, chlorothalonil, copper oxychloride, copper
salts, cymoxanil, cyproconazole, cyprodinil (CGA
219417),(S)-3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-meth-
ylbenzamide (RH 7281), diclocymet (S-2900), diclomezine, dicloran,
difenoconazole,(S)-3,5-dihydro-5-methyl-2-(methylthio)-5-phenyl-3-(phenyl-
amino)-4H-imidazol-4-one (RP 407213), dimethomorph, diniconazole,
diniconazole-M, dodine, edifenphos, epoxiconazole (BAS 480F),
famoxadone, fenamidone, fenarimol, fenbuconazole, fencaramid
(SZX0722), fenpiclonil, fenpropidin, fenpropimorph, fentin acetate,
fentin hydroxide, fluazinam, fludioxonil, flumetover (RPA 403397),
fluquinconazole, flusilazole, flutolanil, flutriafol, folpet,
fosetyl-aluminum, furalaxyl, furametapyr (S-82658), hexaconazole,
ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin,
kresoxim-methyl, mancozeb, maneb, mefenoxam, mepronil, metalaxyl,
metconazole, metominiostrobin/fenominostrobin (SSF-126),
myclobutanil, neo-asozin (ferric methanearsonate), oxadixyl,
penconazole, pencycuron, probenazole, prochloraz, propamocarb,
propiconazole, pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon,
quinoxyfen, spiroxamine, sulfur, tebuconazole, tetraconazole,
thiabendazole, thifuzamide, thiophanate-methyl, thiram,
triadimefon, triadimenol, tricyclazole, trifloxystrobin,
triticonazole, validamycin and vinclozolin; nematocides such as
aldicarb, oxamyl and fenamiphos; bactericides such as streptomycin;
acaricides such as amitraz, chinomethionat, chlorobenzilate,
cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin
oxide, fenpropatlrin, fenpyroximate, hexythiazox, propargite,
pyridaben and tebufenpyrad, and biological agents such as Bacillus
thuringiensis, Bacillus thuringiensis delta endotoxin, baculovirus,
and entomopathogenic bacteria, virus and fungi.
[0364] Preferred insecticides and acaricides for mixing with
compounds of this invention include pyrethroids such as
cypermethrin, cyhalothrin, cyfluthrin and beta-cyfluthrin,
esfenvalerate, fenvalerate and tralomethrin; carbamates such as
fenothicarb, methomyl, oxamyl and thiodicarb; neonicotinoids such
as clothianidin, imidacloprid and thiacloprid, neuronal sodium
channel blockers such as indoxacarb, insecticidal macrocyclic
lactones such as spinosad, abamectin, avermectin and emamectin;
GABA antagonists such as endosulfan and fipronil; insecticidal
ureas such as flufenoxuron and trirlumuron, juvenile hormone mimics
such as diofenolan and pyriproxyphen; pymetrozine; and amitraz.
Preferred biological agents for mixing with compounds of this
invention include Bacillus thuringiensis and Bacillus thuringiensis
delta endotoxin.
[0365] Most preferred mixtures include a mixture of a compound of
this invention with cyhalothrin; a mixture of a compound of this
invention with beta-cyfluthrin; a mixture of a compound of this
invention with esfenvalerate; a mixture of a compound of this
invention with methomyl; a mixture of a compound of this invention
with imidacloprid; a mixture of a compound of this invention with
thiacloprid; a mixture of a compound of this invention with
indoxacarb; a mixture of a compound of this invention with
abamectin; a mixture of a compound of this invention with
endosulfan; a mixture of a compound of this invention with
fipronil; a mixture of a compound of this invention with
flufenoxuron; a mixture of a compound of this invention with
pyriproxyphen; a mixture of a compound of this invention with; a
mixture of a compound of this invention with pymetrozine; a mixture
of a compound of this invention with amitraz; a mixture of a
compound of this invention with Bacillus thuringiensis and a
mixture of a compound of this invention with Bacillus thuringiensis
delta endotoxin.
[0366] In certain instances, combinations with other
arthropodicides having a similar spectrum of control but a
different mode of action will be particularly advantageous for
resistance management.
[0367] Arthropod pests are controlled and protection of agronomic,
horticultural and specialty crops, animal and human health is
achieved by applying one or more of the compounds of this
invention, in an effective amount, to the environment of the pests
including the agronomic and/or nonagronomic locus of infestation,
to the area to be protected, or directly on the pests to be
controlled. Thus, the present invention further comprises a method
for the control of foliar and soil inhabiting arthropods and
nematode pests and protection of agronomic and/or nonagronomic
crops, comprising applying one or more of the compounds of the
invention, or compositions containing at least one such compound,
in an effective amount, to the environment of the pests including
the agronomic and/or nonagronomic locus of infestation, to the area
to be protected, or directly on the pests to be controlled. A
preferred method of application is by spraying. Alternatively,
granular formulations of these compounds can be applied to the
plant foliage or the soil. Other methods of application include
direct and residual sprays, aerial sprays, seed coats,
microencapsulations, systemic uptake, baits, eartags, boluses,
foggers, fumigants, aerosols, dusts and many others. The compounds
can be incorporated into baits that are consumed by the arthropods
or in devices such as traps and the like.
[0368] The compounds of this invention can be applied in their pure
state, but most often application will be of a formulation
comprising one or more compounds with suitable carriers, diluents,
and surfactants and possibly in combination with a food depending
on the contemplated end use. A preferred method of application
involves spraying a water dispersion or refined oil solution of the
compounds. Combinations with spray oils, spray oil concentrations,
spreader stickers, adjuvants, other solvents, and synergists such
as piperonyl butoxide often enhance compound efficacy.
[0369] The rate of application required for effective control will
depend on such factors as the species of arthropod to be
controlled, the pest's life cycle, life stage, its size, location,
time of year, host crop or animal, feeding behavior, mating
behavior, ambient moisture, temperature, and the like. Under normal
circumstances, application rates of about 0.01 to 2 kg of active
ingredient per hectare are sufficient to control pests in agronomic
ecosystems, but as little as 0.001 kg/hectare may be sufficient or
as much as 8 kg/hectare may be required. For nonagronomic
applications, effective use rates will range from about 1.0 to 50
mg/square meter but as little as 0.1 mg/square meter may be
sufficient or as much as 150 mg/square meter may be required.
[0370] The following TEST demonstrates the control efficacy of
compounds of this invention on specific pests. "Control efficacy"
represents inhibition of arthropod development (including
mortality) that causes significantly reduced feeding. The pest
control protection afforded by the compounds is not limited,
however, to these species. See Index Tables A through Q for
compound descriptions. The following abbreviations are used in the
Index Tables which follow: t is tertiary, n is normal, i is iso, c
is cyclo, s is secondary, Me is methyl, Et is ethyl, Pr is propyl,
i-Pr is isopropyl, c-Pr is cyclopropyl, Bu is butyl, s-Bu is
secondary butyl, Pent is pentyl, OMe is methoxy, OEt is ethoxy, SMe
is methylthio, SEt is ethylthio, CN is cyano, NO.sub.2 is nitro,
and Het is heterocycle. The abbreviation "Ex." stands for "Example"
and is followed by a number indicating in which example the
compound is prepared.
20INDEX TABLE A 57 B is O, except where indicated Compound R.sup.1
R.sup.2 R.sup.3 R.sup.4 R.sup.5 and/or R.sup.6 m.p. .degree. C. 1
(Ex 1) H i-Pr H 2-Me 4-OCF.sub.3 207-209 2 H i-Pr H 5-Cl 2-CF.sub.3
195-196 3 H i-Pr H 5-Cl 2-Me-4-CF.sub.3 182-184 4 H i-Pr H 2-Me
4-CF.sub.3 238-240 5 H i-Pr H 2-Me 4-CO.sub.2Me 216-217 6 H i-Pr H
2-Me 3-NO.sub.2 230-233 7 H i-Pr H 2-Me 3-CF.sub.3-4-F 223-225 8 H
i-Pr H 2-Me 3-CN 237-239 9 H i-Pr H 2-Me 2-OCF.sub.3 191-193 10 H
t-Bu H 2-Me 4-OCF.sub.3 163-167 11 H t-Bu H 2-Me 4-CO.sub.2Me
164-169 12 H i-Pr H 2-Cl 4-CO.sub.2Me 224-225 13 H t-Bu H 2-Me
2-OCF.sub.3 203-204 14 H t-Bu H 2-Me 3-NO.sub.2 193-195 15 H t-Bu H
2-Me 3-CF.sub.3-4-F 198-199 16 H i-Pr H 2-OMe 4-OCF.sub.3 178-181
17 H i-Pr H 2-Me 2-OCF.sub.3 170-172 18 H i-Pr H 2-OMe
3-CF.sub.3-4-F 209-211 19 H i-Pr H 2-Cl 4-OCF.sub.3 215-216 20 H
i-Pr Me 2-Me 2-OCF.sub.3 153-155 21 H i-Pr H 5-Me 4-OCF.sub.3
173-175 22 H i-Pr H 5-Me 2-OCF.sub.3 180-185 23 H i-Pr H 5-Me
4-CO.sub.2Me 182-184 24 H i-Pr Me 2-Me 4-OCF.sub.3 Glass 25 H i-Pr
Me 2-Me 4-CO.sub.2Me 67-73 26 H (1,2-di-Me)-Pr H 2-Me 4-OCF.sub.3
189-191 27 H CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-Me 4-OCF.sub.3
147-148 28 H CH.sub.2CH.sub.2OCH.sub.3 H 2-Me 4-OCF.sub.3 153-155
29 H 2-Pent H 2-Me 4-OCF.sub.3 165-168 30 H s-Bu H 2-Me 4-OCF.sub.3
181-183 31 H propargyl H 2-Me 4-OCF.sub.3 190-192 32 H n-Pr H 2-Me
4-OCF.sub.3 189-191 33 H allyl H 2-Me 4-OCF.sub.3 185-187 34 H
Me.sub.2NCH.sub.2CH.sub.2 H 2-Me 4-OCF.sub.3 168-170 35 H propargyl
H 2-Me 4-OCF.sub.3 202-204 36 H i-Bu H 2-Me 4-OCF.sub.3 182-183 37
H i-Pr H 2,4-di-Me 4-OCF.sub.3 205-208 38 H i-Pr H 2,4-di-Me
4-CF.sub.3 >230 39 H i-Pr H 2,4-di-Me 2-OCF.sub.3 231-232 40 H
i-Pr H 2,4-di-Me 4-CO.sub.2Me 219-221 41 H i-Pr H 2,4-di-Me
3-CF.sub.3-4-F 222-224 42 H t-Bu H 2-OMe 4-CF.sub.3 210-214 43 H
t-Bu H 2-OMe 4-OCF.sub.3 170-173 44 H i-Pr Me 2-Me 3-NO.sub.2 Oil
45 H i-Pr H 2-Cl 4-OCF.sub.3 187-194 46 H t-Bu H 2-Cl 4-OCF.sub.3
205-207 47 H allyl H 2-Cl 4-OCF.sub.3 188-189 48 H s-Bu H 2-Cl
4-OCF.sub.3 192-193 49 H --CH.sub.2CH.sub.2CH.sub.2CH.sub.2-- 2-Me
4-OCF.sub.3 138-142 50 H CH.sub.2CF.sub.3 H 2-Me 4-OCF.sub.3
>230 51 H c-Bu H 2-Me 4-OCF.sub.3 218-220 52 (Ex 3) H i-Pr H
2-Me 2-Me-4-CF.sub.3 247-248 53 H i-Pr H 5-Me 2-Me-4-CF.sub.3
186-188 54 H i-Pr H H 4-OCF.sub.3 185-187 55 H i-Pr H H 3-NO.sub.2
199-200 56 H i-Pr H H 2-OCF.sub.3 118-122 57 Me i-Pr H H
4-OCF.sub.3 117-118 58 Me i-Pr H H 3-NO.sub.2 134-136 59 Me i-Pr H
H 2-OCF.sub.3 128-130 60 H i-Pr H H 3-CF.sub.3 176-177 61 H i-Pr H
H 2-Me-4-CF.sub.3 100-106 62 H Me H 2-Me 4-OCF.sub.3 204-206 63 H
Et H 2-Me 4-OCF.sub.3 198-200 64 H NHi-Pr H 2-Me 4-OCF.sub.3
126-128 65 H i-Pr H 2-Me 3-CF.sub.3 198-200 66 H i-Pr H 2-Me 4-CN
>230 67 H i-Pr H 2-Me 2-NO.sub.2 >230 68 H i-Pr H 2-Me
3,5-di-CF.sub.3 >230 69 H i-Pr H 2-Me 4-NO.sub.2 227-230 70 H
i-Pr H 2-Me 2-CF.sub.3 227-230 71 H i-Pr H H 2-Me-4-OCF.sub.3
118-124 72 H i-Pr H H 4-CF.sub.3 196-198 73 H i-Pr H 2-Me
2-Me-4-SCF.sub.2H 212-213 74 H t-Bu H 2-Me 2-Me-4-SCF.sub.2H
193-195 75 H i-Pr H 2-Me 2-Me-4-OCF.sub.3 221-222 76 H t-Bu H 2-Me
4-CF.sub.3 217-219 77 H t-Bu H 2-Me 3-CF.sub.3 197-198 78 H t-Bu H
2-Me 3,5-di-CF.sub.3 206-207 79 H t-Bu H 2-Me 4-CN >230 80 H
t-Bu H 2-Me 4-NO.sub.2 >230 81 Me i-Pr H 2-Me 2-CF.sub.3 oil 82
Me i-Pr H 2-Me 4-OCF.sub.3 151-157 83 Me i-Pr H H 2-Me-4-OCF.sub.3
103-107 84 Me t-Bu H 2-Me 2-Me-4-CF.sub.3 233-234 85 H t-Bu H 2-Me
2-Me-4-OCF.sub.3 207-209 86 H t-Bu H 2-Me 2,5-di-CF.sub.3 199-201
87 H i-Pr H 2-CF3 4-OCF.sub.3 183-185 88 H i-Pr H 2-CF3 4-CF.sub.3
211-212 89 H t-Bu H 2-CF.sub.3 4-CF.sub.3 191-192 90 H R-(-)-s-Bu H
2-Me 4-OCF.sub.3 170-172 91 H S-(+)-s-Bu H 2-Me 4-OCF.sub.3 177-179
92 Me i-Pr H H 4-CF.sub.3 oil 93 Me i-Pr H 2-OCF.sub.2H 4-OCF.sub.3
162-164 94 H t-Bu H 2-CF.sub.3 4-OCF.sub.3 145-148 95 H i-Pr Me
2-CF.sub.3 4-CF.sub.3 151-154 96 H i-Pr Me 2-CF.sub.3 4-OCF.sub.3
140-144 97 H i-Pr H 2-OCF.sub.2H 4-CF.sub.3 224-227 98 H i-Pr H
2,4-di-Me 2-Me-4-CF.sub.3 >230 99 H i-Pr H 2-Cl 2-Me-4-CF.sub.3
>230 100 H CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-Cl 2-Me-4-CF.sub.3
194-197 101 H s-Bu H 2-Cl 2-Me-4-CF.sub.3 212-214 102 H c-Pr H 2-Me
4-OCF.sub.3 208-210 103 H CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2,4-di-Me
4-OCF.sub.3 166-168 104 H CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2,4-di-Me
4-CF.sub.3 192-194 105 H i-Pr H 4-Me 4-CF.sub.3 212-213 106 H i-Pr
H 4-Me 4-OCF.sub.3 204-205 107 H i-Pr H 2-Br-4-Me 4-OCF.sub.3
>230 108 H t-Bu H 2-Br-4-Me 4-OCF.sub.3 118-120 109 H i-Pr H
2-NO.sub.2 4-CF.sub.3 203-204 110 H t-Bu H 2-NO.sub.2 4-CF.sub.3
199-200 111 H i-Pr H 2-NO.sub.2 4-OCF.sub.3 204-205 112 H t-Bu H
2-NO.sub.2 4-OCF.sub.3 181-183 113 H i-Pr H 2-Me
2-Me-4-S(O).sub.2CF.sub.2H 218-221 114 H i-Pr H 2-Me
2-Me-4-S(O)CF.sub.2H 203-206 115 H CH(CH.sub.3)CH.sub.2OCH.sub.3 H
3-Cl 4-CF.sub.3 158-161 116 H i-Pr H 4-Br 4-CF.sub.3 232-234 117 H
t-Bu H 4-Br 4-CF.sub.3 204-206 118 H CH(CH.sub.3)CH.sub.2OCH.sub.3
H 4-Br 4-CF.sub.3 157-158 119 H i-Pr H 4-Br 4-OCF.sub.3 221-222 120
H t-Bu H 4-Br 4-OCF.sub.3 173-175 121 H
CH(CH.sub.3)CH.sub.2OCH.sub.3 H 4-Br 4-OCF.sub.3 153-155 122 H
CH(CH.sub.3)CH.sub.2OCH.sub.3 H 3-Cl 4-OCF.sub.3 137-140 123 H i-Pr
H 4-F 4-CF.sub.3 205-206 124 H t-Bu H 2-Cl 2-Me-4-CF.sub.3 237-240
125 H 2-Pent H 2-Me 4-CF.sub.3 194-196 126 H s-Bu H 2-Me 4-CF.sub.3
207-210 127 H Et H 2-Me 4-CF.sub.3 >240 128 H Me H 2-Me
4-CF.sub.3 236-237 129 H i-Pr H 4-F 4-OCF.sub.3 208-209 130 H
CH(CH.sub.3)CH.sub.2OCH.sub.3 H 4-F 4-OCF.sub.3 151-152 131 H
CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-Me 4-CF.sub.3 188-190 132
CH.sub.2CO.sub.2Me i-Pr H H 4-CF.sub.3 oil 133 CH.sub.2CO.sub.2Me
i-Pr H H 4-OCF.sub.3 oil 134 Me Et H 2-Me 4-CF.sub.3 oil 135 Me Et
H 2-Me 4-OCF.sub.3 oil 136 Me Et H 2-Me 2-Me-4-SCF.sub.2H 132-136
137 H CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-Me-4-Br 4-CF.sub.3 197-199
138 H CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-Me-4-Br 4-OCF.sub.3 188-190
139 H i-Pr H 3-Cl 4-CF.sub.3 201-202 140 H t-Bu H 3-Cl 4-CF.sub.3
159-161 141 H i-Pr H 3-Cl 4-OCF.sub.3 190-192 142 H t-Bu H 3-Cl
4-OCF.sub.3 150-152 143 H iPr H 2-Br-4-Me 4-CF.sub.3 >230 144 H
t-Bu H 2-Br-4-Me 4-CF.sub.3 213-215 145 H
CH(CH.sub.3)CH.sub.2OCH.sub.3 H 5-F 4-CF.sub.3 145-147 146 H 58 H
2-Me 4-CF.sub.3 >230 147 H i-Pr H 2-Me 2-F-4-CF.sub.3 224-226
148 H i-Pr H 2-Me 2-CF.sub.3-4-F 223-225 149 H t-Bu H 4-F
4-OCF.sub.3 180-187 150 H CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-Me
2-Me-4-CF.sub.3 194-197 151 H Me H 2-Me 2-Me-4-CF.sub.3 >230 152
H Et H 2-Me 2-Me-4-CF.sub.3 243-245 153 H 59 H 2-Me 2-Me-4-CF.sub.3
>230 154 H i-Pr H 3-NO.sub.2 4-CF.sub.3 244-246 155 H i-Pr H
3-NO.sub.2 4-OCF.sub.3 239-240 156 H t-Bu H 3-NO.sub.2 4-OCF.sub.3
180-184 157 H CH(CH.sub.3)CH.sub.2OCH.sub.3 H 3-NO.sub.2
4-OCF.sub.3 172-175 158 H t-Bu H 3-NO.sub.2 4-CF.sub.3 194-196 159
H CH(CH.sub.3)CH.sub.2OCH.sub.3 H 3-NO.sub.2 4-CF.sub.3 178-179 160
H i-Pr H 2-Cl 4-CF.sub.3 >230 161 H
CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-Cl 4-CF.sub.3 182-185 162 H t-Bu
H 5-Cl 2-Me-4-CF.sub.3 203-205 163 H CH(CH.sub.3)CH.sub.2OCH.sub.3
H 5-Cl 2-Me-4-CF.sub.3 154-155 164 H i-Pr H 2-Me
2,4-(CF.sub.3).sub.2 >230 165 H i-Pr H 2-Me 3,4-OCF.sub.2O--
199-200 166 H CH.sub.2CN H 2-Me 4-CF.sub.3 218-223 167 H
CH(CH.sub.3)Ph H 2-Me 4-CF.sub.3 225-228 168 H CH(CH.sub.3)Ph H
2-Me 4-OCF.sub.3 208-210 169 H t-Bu H 2-Cl 4-CF.sub.3 191-193 170 H
i-Pr Me 2-Cl 4-CF.sub.3 136-140 171 H i-Pr H 2-Me
4-SO.sub.2CH.sub.3 >250 172 H i-Pr H 5-Cl 4-CF.sub.3 217-218 173
H t-Bu H 5-Cl 4-CF.sub.3 231-235 174 H
CH(CH.sub.3)CH.sub.2OCH.sub.3 H 5-Cl 4-CF.sub.3 175-177 175 H i-Pr
H 4-I 4-CF.sub.3 >230 176 H t-Bu H 4-I 4-CF.sub.3 215-219 177 H
CH(CH.sub.3)CH.sub.2OCH.sub.3 H 4-I 4-CF.sub.3 173-178 178 H i-Pr H
4-I 4-OCF.sub.3 >230 179 H t-Bu H 4-I 4-OCF.sub.3 192-194 180 H
CH(CH.sub.3)CH.sub.2OCH.sub.3 H 4-I 4-OCF.sub.3 178-180 181 H
CH.sub.2(3-pyridinyl) H 2-Me 4-CF.sub.3 198-199 182 H CH.sub.2CN H
2-Me 2-Me-4-CF.sub.3 >230 183 H CH(CH.sub.3)CO.sub.2CH.sub.3 H
2-Me 4-CF.sub.3 223-225 184 H i-Pr H 2-F 4-CF.sub.3 228-229 185 H
i-Pr H 5-F 4-CF.sub.3 169-170 186 H i-Pr H 2-F 2-Me-4-OCF.sub.3
206-208 187 H i-Pr H 5-F 2-Me-4-OCF.sub.3 125-126 188 H i-Pr H 2-F
2-Me-4-CF.sub.3 234-235 189 H i-Pr H 5-F 2-Me-4-CF.sub.3 133-135
190 H CH.sub.2(3-pyridinyl) H 2-Me 4-OCF.sub.3 201-202 191 H
CH.sub.2CH.sub.2SCH.sub.3 H 2-Me 4-CF.sub.3 187-188 192 H
CH.sub.2CH.sub.2SCH.sub.3 H 2-Me 2-Me-4-CF.sub.3 250-251 193 H
CH.sub.2CH.sub.2SEt H 2-Me 4-CF.sub.3 190-191 194 H
CH.sub.2CH.sub.2SEt H 2-Me 2-Me-4-CF.sub.3 228-230 195 H
CH(CH.sub.3)CH.dbd.CH.sub.2 H 2-Me 2-Me-4-CF.sub.3 211-214 196 H
i-Pr H 2-Et 4-CF.sub.3 228-230 197 H CH(CH.sub.3)CH.sub.2OCH.sub.3
H 2-Et 4-CF.sub.3 176-177 198 H i-Pr H 2-Me
3,4-OCF.sub.2CF.sub.2O-- 218-220 199 H i-Pr H 2-Me
2-(CONMe.sub.2-4,5-Cl.sub.2 229-230 200 H i-Pr H 2-Me
2-(CO-1-piperidinyl)- 202-205 4,5-Cl.sub.2 201 H t-Bu H 2-Et
4-CF.sub.3 187-191 202 H CH(CH.sub.3)CH.sub.2SCH.sub.3 H 2-Et
2-Me-4-CF.sub.3 206-208 203 H i-Pr H 2-Me 2-(CONMe.sub.2)-4-Br
191-194 204 H i-Pr H 2-Me 2-(CONMe.sub.2)-5-Br 190-194 205 H
CH(CH.sub.3)CH.sub.2SO.sub.2CH.- sub.3 H 2-Me 2-Me-4-CF.sub.3
231-233 206 H c-Pr H 2-Me 2-Me-4-CF.sub.3 258-261 207 H c-Pr H 2-Cl
2-Me-4-CF.sub.3 >260 208 H i-Pr H 2-I 2-Me-4-OCF.sub.3 241-242
209 H i-Pr H 2-I 2-Me-4-CF.sub.3 260-262 210 H i-Pr H 2-Me
2-(CONMe.sub.2)-4-F 164-170 211 H i-Pr H 2-Me 2-(CONMe.sub.2)-5-F
167-171 212 H i-Pr H 2-Me 2-(CO-1-piperidinyl)-4- 105-117 Br 213 H
CH(CH.sub.3)CH.sub.2OH H 2-Me 2-Me-4-CF.sub.3 179-180 214 H
CH(CH.sub.3)CH.sub.2OH H 2-Cl 2-Me-4-CF.sub.3 183-185 215 H i-Pr H
2-Cl 2-(CONMe.sub.2)-4-Br 165-170 216 H i-Pr H 2-Cl
2-(CONMe.sub.2)-5-Br 179-181 217 H i-Pr H 2-Me
2-(3-CF.sub.3-1-pyrazolyl)-4- 243-244 CF.sub.3 218 H i-Pr H 2-Me
2-(1-(1,2,4-triazolyl))-4- 238-240 CF.sub.3 219 H i-Pr H 2-Me
2-(3-Br-1-pyrazolyl)-4- >250 CF.sub.3 220 H i-Pr H 2-Me
2-(3-CN-1-pyrazolyl)-4- >250 CF.sub.3 221 H i-Pr H 2-Me
2-(4-CF.sub.3-1-imidazolyl)- >250 4-CF.sub.3 222 H i-Pr H 2-Me
2-(3-CH.sub.3-1-pyrazolyl)- 248-250 4-CF.sub.3 223 H i-Pr H 2-Me
2-(2-CH.sub.3-1-imidazolyl)- 186-188 4-CF.sub.3 224 H i-Pr H 2-Me
2-(3-CF3-1-(1,2,4- 254-256 triazolyl))-4-CF.sub.3 225 H i-Pr H 2-Me
2-(1-pyrazolyl)-4-CF.sub.3 246-248 226 H i-Pr H 2-Me
2-(3-CO.sub.2Et-5-Me-1- 224-225 pyrazolyl)-4-CF.sub.3 227 H i-Pr H
2-Me 2-(1-imidazolyl)-4-CF.sub.- 3 240-241 228 H i-Pr H 2-Me
2-(3-CF.sub.3-5-Me-1- 229-231 pyrazolyl)-4-CF.sub.3 229 H i-Pr H
2-Me 2-(3,5-Me.sub.2-1-pyrazo- lyl)- 214-218 4-CF.sub.3 230 H i-Pr
H 2-Me 2-(2,4-Me.sub.2-1- 246-248 imdazolyl)-4-CF.sub.3 231 H i-Pr
H 2-Me 2-(4-Me-1-imidazolyl)- 223-225 4-CF.sub.3 232 H i-Pr H 2-Cl
2-(3-CF.sub.3-1-pyrazolyl)-4- >250 CF.sub.3 233 H i-Pr H 2-Cl
2-(1-(1,2,4-triazolyl))-4- 252-254 CF.sub.3 234 H i-Pr H 2-Cl
2-(3-Br-1-pyrazolyl)-4- >250 CF.sub.3 235 H i-Pr H 2-Cl
2-(3-CO.sub.2Et-5-Me-1- 220-221 pyrazolyl)-4-CF.sub.3 236 H i-Pr H
2-Cl 2-(4-CO.sub.2Me-1- 255-257 imidazolyl)-4-CF.sub.3 237 H i-Pr H
2-Cl 2-(3-CN-1-pyrazolyl)-4- >250 CF.sub.3 238 H i-Pr H 2-Cl
2-(1-imidazolyl)-4-CF.sub.3 248-249 239 H i-Pr H 2-Me
2-(4-CO.sub.2Me-1- 219-222 imidazolyl)-4-CF.sub.3 240 H i-Pr H 2-Me
2-(2-thienyl)-4-CF.sub.3 241-243 241 H i-Pr H 2-Me
2-(3-thienyl)-4-CF.sub.3 229-231 242 H i-Pr H 2-Me
2-(2-furanyl)-4-CF.sub.3 246-247 243 H i-Pr H 2-Me
2-(3-t-Bu-1-pyrazolyl)-4- 247-249 CF.sub.3 244 H i-Pr H 2-Me
2-(3-s-Bu-1-pyrazolyl)- 224-225 4-CF.sub.3 245 H i-Pr H 2-Me
2-(3-c-Pr-1-pyrazolyl)-4- 220-221 CF.sub.3 246 H i-Pr H 2-Me
2-(3-Me-5-isoxazolyl)-4- 233-234 CF.sub.3 247 H i-Pr H 2-Me 2-
60-4-CF.sub.3 >250 248 H i-Pr H 2-Me 2-(CONMe.sub.2)-4-CF.sub.3
188-192 249 H i-Pr H 2-Me 2-(CONMe.sub.2)-5-CF.sub.3 194-196 250 H
i-Pr H 2-Me 2-(CO-1-pyrrolidinyl)-4- 201-204 CF.sub.3 251 H i-Pr H
2-Me 2-(CO-1-pyrrolidinyl)-5- 221-223 CF.sub.3 252 H i-Pr H 2-Me
2-OCH.sub.3-4-CF.sub.3 188-189 253 H i-Pr H 2-Me
2-(3-Cl-5-isoxazolyl)-4- 247-248 CF.sub.3 254 H i-Pr H 2-Me
2-Oi-Pr-4-CF.sub.3 158-159 255 H i-Pr H 2-Cl
2-(4-Me-1-pyrazolyl)-4- 252-253 CF.sub.3 256 H i-Pr H 2-Me
2-(4-Me-1-pyrazolyl)-4- 226-227 CF.sub.3 257 H i-Pr H 2,5-Cl.sub.2
2-Me-4-CF.sub.3 235-237 258 H i-Pr H 2-Me 4-Ph 221-224 259 H i-Pr H
2-Me 4-(4-OCH.sub.3)Ph >230 260 H i-Pr H 2-Me 4-(2-Me)Ph 156-158
261 H i-Pr H 2-Me 4-(3-CH.sub.3)Ph 225-226 262 H i-Pr H 2-Me
4-(3-CF.sub.3)Ph 214-215 263 H i-Pr H 2-Me 4-(4-F)Ph >230 264 H
--CH.sub.2CH.sub.2CH.sub.2CH.s- ub.2-- 2-Cl 3-Cl 158-161 265 H 61 H
2-Me 4-OCF.sub.3 >230 266 H i-Pr H 2-CF.sub.3 2-Me-4-Br >230
267 H t-Bu H 2-CF.sub.3 2-Me-4-Br 234-236 268 H i-Pr Me 2-CF.sub.3
2-Me-4-Br 154-158 269 H CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-CF.sub.3
2-Me-4-Br 202-204 270 H s-Bu H 2-CF.sub.3 2-Me-4-Br >230 271 H
s-pentyl H 2-CF.sub.3 2-Me-4-Br 215-217 272 H i-Pr H 2-CH.sub.3
2-Me-4-CF.sub.3 >230 273 H i-Pr Me 2-OCHF.sub.2 2-Me-4-Br
224-227 274 H i-Pr H 2-CH.sub.3 2-(CONMe.sub.2)-4-CF.sub- .3
130-137 275 B is S H i-Pr H 2-Me 2-Me-4-CF.sub.3 193-195 276 H i-Pr
H 2-Cl 2-(1-pyrazolyl)-4-CF.sub.3 249-250 277 B is S H i-Pr H 2-Me
4-OCF.sub.3 169-171 278 B is S H i-Pr H 2-Me 4-CF.sub.3Ph
204-206
[0371]
21INDEX TABLE B 62 R.sup.7(c) is H, except where indicated and B is
O, except where indicated Compound R.sup.2 R.sup.3 (R.sup.4).sub.n
R.sup.7(a) R.sup.7(b) m.p. .degree. C. B1 (Ex. 4) i-Pr H 2-Me
CF.sub.3 CH.sub.3 247-248 B2 i-Pr H 2-Me OCH.sub.2CF.sub.3 H
188-191 B3 i-Pr H 2-Cl CF.sub.3 CH.sub.3 234-236 B4 t-Bu H 2-Cl
CF.sub.3 CH.sub.3 243-245 B5 CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-Cl
CF.sub.3 CH.sub.3 198-201 B6 CH(CH.sub.3)CH.dbd.CH.sub.2 H 2-Me
CF.sub.3 CH.sub.3 226-227 B7 i-Pr H 2-Cl OCH.sub.2CF.sub.3 H
208-210 B8 t-Bu H 2-Cl OCH.sub.2CF.sub.3 H 174-175 B9
CH(CH.sub.3)CH.sub.2OCH.sub.- 3 H 2-Cl OCH.sub.2CF.sub.3 H 163-165
B10 i-Pr H 2-Me CF.sub.3 H 208-211 B11
CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-Me CF.sub.3 CH.sub.3 187-191 B12
s-Bu H 2-Me CF.sub.3 CH.sub.3 215-218 B13 2-pentyl H 2-Me CF.sub.3
CH.sub.3 213-215 B14 i-Pr H 2-Me Cl H 235-237 B15 i-Pr H 2-Me H Cl
235-237 B16 i-Pr H 2-OCHF.sub.2 CF.sub.3 CH.sub.3 221-224 B17 i-Pr
H 2-Me CF.sub.2CF.sub.3 CH.sub.3 208-209 B18 t-Bu H 2-Me
CF.sub.2CF.sub.3 CH.sub.3 211-212 B19 CH(CH.sub.3)CH.sub.2OCH.sub.3
H 2-Me CF.sub.2CF.sub.3 CH.sub.3 193-196 B20 t-Bu H 2-CF.sub.3
CF.sub.3 CH.sub.3 >250 B21 t-Bu H 2-CF.sub.3 CF.sub.3 CH.sub.3
218-222 B22 CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-CF.sub.3 CF.sub.3
CH.sub.3 200-202 B23 i-Pr H 2-Me CF.sub.3 Br 253-255 B24
CH(CH.sub.3)CH.sub.2SCH.sub.3 H 2-Me CF.sub.3 CH.sub.3 222-223 B25
CH(CH.sub.3)CH.sub.2CN H 2-Me CF.sub.3 CH.sub.3 230-232 B26
CH.sub.2CH.sub.2CN H 2-Me CF.sub.3 CH.sub.3 >260 B27 c-Pr H 2-Me
CF.sub.3 CH.sub.3 >260 B28 i-Pr H 2-Me CF.sub.3 OCH.sub.3
181-183 B29 i-Pr H 2-Me Cl CH.sub.3 246-247 B30 i-Pr H 2-Me
CF.sub.3 Ph >250 B31 i-Pr H 2-I CF.sub.3 CH.sub.3 256-257 B32
i-Pr H 2-F CF.sub.3 CH.sub.3 218-220 B33 i-Pr H 5-F CF.sub.3
CH.sub.3 144-146 B34 CH(CH.sub.3)CH.sub.2SO.sub.2CH.sub.3 H 2-Me
CF.sub.3 CH.sub.3 243-245 B35 CH(CH.sub.3)CH.sub.2OH H 2-Me
CF.sub.3 CH.sub.3 222-223 B36 CH(CH.sub.3)CH.sub.2CO.sub.2CH.sub.3
H 2-Me CF.sub.3 CH.sub.3 204-206 B37 i-Pr H 2-Me CF.sub.3
CH.sub.2OCH.sub.3 241-242 B38 i-Pr H 2-Me CF.sub.3 CH.sub.2CH.sub.3
229-231 B39 i-Pr H 2-Me CH.sub.3 Cl 236-237 B40 i-Pr H 2-Me
CH.sub.3 2-pyridinyl 278-281 B41 t-Bu H 2-Me CF.sub.3 CH.sub.3
234-236 B42 i-Pr H 2-Me CF.sub.3 n-Pr 224-226 B43 i-Pr Me 2-Me
CF.sub.3 CH.sub.3 202-205 B44 i-Pr H 2-Me c-Pr CH.sub.3 226-229 B45
i-Pr H 2-Me c-Pr CH.sub.3, HCl salt >230 B46 i-Pr H 2-Me
CF.sub.3 Cl 248-254 B47 i-Pr H 2-Me CF.sub.3 i-Pr 235-237 B48 i-Pr
H 2-Me CF.sub.3 1-(1,2,4-triazolyl) >260 B49 i-Pr H 2-Br
CF.sub.3 CH.sub.3 247-248 B50 i-Pr H 2-Me OCH.sub.2CF.sub.3
CH.sub.3 150-160 B51 i-Pr H 2-Me CF.sub.3 2-phenoxy 231-232 B52
i-Pr H 2-Me CF.sub.3 1-morpholinyl >250 B53 i-Pr H 2-Me CF.sub.3
1-(3-CF.sub.3-imidazolyl) 247-250 B54 i-Pr H 2-Me CF.sub.3
1-(3-Br-pyrazolyl) >260 B55 i-Pr H 2-Me CF.sub.3
1-(3-CF.sub.3-pyrazolyl) >260 B56 i-Pr H 2-Me CF.sub.3
1-((3-CF.sub.3)-1,2,4-triazolyl) >260 B57 i-Pr H 2-Me CF.sub.3
1-((3-CN)-1,2,4-triazolyl) >260 B58 i-Pr H 2-Me i-Bu Cl 185-190
B59 i-Pr H 2-Me CF.sub.3 2-MePh 200-203 B60 i-Pr H 2-Me i-Pr
CH.sub.3 186-190 B61 i-Pr H 2-Me Ph Cl 229-234 B62 i-Pr H 2-Me
CF.sub.3 SCH.sub.2CH(CH.sub.3).sub.2 230-231 B63 i-Pr H 2-Me
CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 209-211 B64 i-Pr H 2-Me CF.sub.3
1-pyrazolyl >250 B65 i-Pr H 2-Me CF.sub.2CF.sub.3 H >250 B66
i-Pr H 2-Me CF.sub.2CF.sub.3 i-Pr 209-212 B67 i-Pr H 2-Me, 4-Br
CF.sub.3 CH.sub.3 >250 B68 i-Pr H 2-Me OCH.sub.2CF.sub.3 n-Pr
165-169 B69 i-Pr H 2-Me Cl n-Pr 200-205 B70 i-Pr H 2-Me Cl Et
200-205 B71 i-Pr H 2-Me CF.sub.3 CN 214-215 B72 i-Pr H 2,5-Cl.sub.2
CF.sub.3 CH.sub.3 >240 B73 i-Pr H 2-Me H H, R.sup.7(c) is SPh
223-225 B74 B is S, i-Pr H 2-Me CF.sub.3 CH.sub.3 201-203 B75 B is
S, i-Pr H 2-Me CF.sub.3 Et 173-175 B76 B is S, i-Pr H 2-Me
CF.sub.2CF.sub.3 CH.sub.3 156-158 B77 i-Pr H 2-Me H
1-((3-CF.sub.3)-pyrazolyl) 224-225 B78 i-Pr H 2-Me CF.sub.3 2-ClPh
223-225
[0372]
22INDEX TABLE C 63 B is O, except where indicated Compound R.sup.2
R.sup.3 (R.sup.4).sub.n R.sup.7(a) R.sup.7(b) m.p. .degree. C. C1
(Ex. 5) i-Pr H 2-Me CF.sub.3 CH.sub.3 252-253 C2 i-Pr H 2-Cl
CF.sub.3 CH.sub.3 260-262 C3 i-Pr H 2-Me CF.sub.3 OCH.sub.3 195-196
C4 i-Pr H 2-Me CF.sub.3 N(CH.sub.3).sub.2 270-272 C5 i-Pr H 2-Me
CF.sub.3 Et 246-248 C6 i-Pr H 2-Me CF.sub.3 Ph 175-177 C7 i-Pr H
2-Me i-Pr Et 179-182 C8 i-Pr H 2-Me c-Pr Et 202-204 C9 i-Pr H 2-Me
i-Pr CH.sub.3 206-209 C10 i-Pr H 2-Me c-Pr CH.sub.3 222-225 C11
i-Pr H 2-Me c-Pr Ph 236-239 C12 i-Pr H 2-Me CF.sub.3 SCH.sub.3
244-247 C13 i-Pr H 2-Me CF.sub.3 1-pyrrolidinyl 272-273 C14 i-Pr H
2-Me CF.sub.3 OCH.sub.2C(Cl).dbd.CH.sub.2 142-144 C15 Et H 2-Me
CF.sub.3 2-MePh 253-256 C16 i-Pr H 2-Me CF.sub.3 2-MePh 244-246 C17
t-Bu H 2-Me CF.sub.3 2-MePh 251-253 C18 Et H 2-Cl CF.sub.3 2-MePh
242-243 C19 i-Pr H 2-Cl CF.sub.3 2-MePh 237-240 C20 t-Bu H 2-Cl
CF.sub.3 2-MePh 253-255 C21 Et H 2-Me CF.sub.3 2-ClPh 251-252 C22
i-Pr H 2-Me CF.sub.3 2-ClPh 246-248 C23 t-Bu H 2-Me CF.sub.3 2-ClPh
238-239 C24 Et H 2-Cl CF.sub.3 2-ClPh 248-249 C25 i-Pr H 2-Cl
CF.sub.3 2-ClPh 254-255 C26 t-Bu H 2-Cl CF.sub.3 2-ClPh 240-242 C27
Et H 2-Me CF.sub.3 c-Pr 236-238 C28 i-Pr H 2-Me CF.sub.3 c-Pr
240-241 C29 t-Bu H 2-Me CF.sub.3 c-Pr 246-248 C30 Et H 2-Cl
CF.sub.3 c-Pr 240-242 C31 i-Pr H 2-Cl CF.sub.3 c-Pr 232-235 C32
t-Bu H 2-Cl CF.sub.3 c-Pr 266-268 C33 Et H 2-Me CF.sub.3 i-Pr
230-231 C34 i-Pr H 2-Me CF.sub.3 i-Pr 211-214 C35 t-Bu H 2-Me
CF.sub.3 i-Pr 210-213 C36 Et H 2-Cl CF.sub.3 i-Pr 247-249 C37 i-Pr
H 2-Cl CF.sub.3 i-Pr 236-239 C38 t-Bu H 2-Cl CF.sub.3 i-Pr 235-238
C39 Et H 2-Me CF.sub.2CF.sub.3 2-MePh 247 C40 i-Pr H 2-Me
CF.sub.2CF.sub.3 2-MePh 218-220 C41 t-Bu H 2-Me CF.sub.2CF.sub.3
2-MePh 224-226 C42 Et H 2-Cl CF.sub.2CF.sub.3 2-MePh 241-243 C43
i-Pr H 2-Cl CF.sub.2CF.sub.3 2-MePh 232-234 C44 t-Bu H 2-Cl
CF.sub.2CF.sub.3 2-MePh 237-239 C45 Et H 2-Me CF.sub.2CF.sub.3
2-ClPh 255-257 C46 i-Pr H 2-Me CF.sub.2CF.sub.3 2-ClPh 224 C47 t-Bu
H 2-Me CF.sub.2CF.sub.3 2-ClPh 215 C48 Et H 2-Cl CF.sub.2CF.sub.3
2-ClPh 248-250 C49 i-Pr H 2-Cl CF.sub.2CF.sub.3 2-ClPh 222-224 C50
t-Bu H 2-Cl CF.sub.2CF.sub.3 2-ClPh 242 C51 Et H 2-Me
CF.sub.2CF.sub.3 Ph 246-248 C52 i-Pr H 2-Me CF.sub.2CF.sub.3 Ph 220
C53 t-Bu H 2-Me CF.sub.2CF.sub.3 Ph 242 C54 Et H 2-Cl
CF.sub.2CF.sub.3 Ph 238-240 C55 i-Pr H 2-Cl CF.sub.2CF.sub.3 Ph 260
C56 t-Bu H 2-Cl CF.sub.2CF.sub.3 Ph 231-232 C57 i-Pr H 2-Me
CF.sub.2CF.sub.3 CH.sub.3 208 C58 t-Bu H 2-Me CF.sub.2CF.sub.3
CH.sub.3 242-244 C59 Et H 2-Cl CF.sub.2CF.sub.3 CH.sub.3 210-212
C60 i-Pr H 2-Cl CF.sub.2CF.sub.3 CH.sub.3 195 C61 t-Bu H 2-Cl
CF.sub.2CF.sub.3 CH.sub.3 246-248 C62 Et H 2-Me CF.sub.2CF.sub.3
c-Pr 224-225 C63 i-Pr H 2-Me CF.sub.2CF.sub.3 c-Pr 232-234 C64 Et H
2-Cl CF.sub.2CF.sub.3 c-Pr 216-218 C65 i-Pr H 2-Cl CF.sub.2CF.sub.3
c-Pr 218-220 C66 t-Bu H 2-Cl CF.sub.2CF.sub.3 c-Pr 210-212 C67 Et H
2-Me CF.sub.2CF.sub.3 i-Pr 218-220 C68 i-Pr H 2-Me CF.sub.2CF.sub.3
i-Pr 196-198 C69 t-Bu H 2-Me CF.sub.2CF.sub.3 i-Pr 212-214 C70 Et H
2-Cl CF.sub.2CF.sub.3 i-Pr 216-220 C71 i-Pr H 2-Cl CF.sub.2CF.sub.3
i-Pr 215-218 C72 t-Bu H 2-Cl CF.sub.2CF.sub.3 i-Pr 240-244 C73 i-Pr
H 2-Me CF.sub.2CF.sub.3 Et 210-212 C74 Et H 2-Me CF.sub.2CF.sub.3
Et 230-232 C75 Et H 2-Cl CF.sub.2CF.sub.3 Et 210-213 C76 i-Pr H
2-Cl CF.sub.2CF.sub.3 Et 203-204 C77 t-Bu H 2-Cl CF.sub.2CF.sub.3
Et 230-232 C78 Et H 2-Me CF.sub.2CF.sub.3 CH.sub.3 238-240 C79 B is
S i-Pr H 2-Me CF.sub.3 Et 190-193 C80 i-Pr H 2-Me CF.sub.3
2-CF.sub.3Ph 255-258
[0373]
23INDEX TABLE D 64 R.sup.7 (c) is H, except where indicated and B
is O, except where indicated Compound R.sup.2 R.sup.3
(R.sup.4).sub.n R.sup.7(a) R.sup.7(b) m.p. .degree. C. D1 i-Pr H
2-Me CF.sub.3 CH.sub.3 200-204 D2 (Ex. 2) i-Pr H 2-Me CF.sub.3 Et
123-126 D3 i-Pr H 2-Cl CF.sub.3 CH.sub.3 233-235 D4 t-Bu H 2-Me
CF.sub.3 Et 215-218 D5 i-Pr H 2-Me CH.sub.3 Ph 238-239 D6 i-Pr H
2-Me CH.sub.3 CH.sub.3 206-208 D7 i-Pr H 2-Me CH.sub.3
CH.sub.2CF.sub.3 246-248 D8 i-Pr H 2-Cl Et CF.sub.3 235-237 D9 i-Pr
H 2-Me CH.sub.3 CH.sub.3, R.sup.7 (c) is Cl 205-207 D10 i-Pr H 2-Me
CH.sub.3 4-CF.sub.3Ph 256-258 D11 i-Pr H 2-Me CH.sub.3 2-CF.sub.3Ph
204-206 D12 t-Bu H 2-Me CH.sub.3 Ph 236-238 D13 i-Pr H 2-F CH.sub.3
Ph 227-229 D14 i-Pr H 5-F CH.sub.3 Ph 209-211 D15 i-Pr H 2-Cl
CH.sub.3 Ph 233-234 D16 i-Pr H H CH.sub.3 Ph 215-217 D17 i-Pr H
2-NO.sub.2 CH.sub.3 Ph 236-237 D18 i-Pr H 2-Cl CF.sub.3 Ph 240-242
D19 (Ex. 6) i-Pr H 2-Me CF.sub.3 Ph 260-262 D20 i-Pr H 2-I CH.sub.3
Ph 250-251 D21 i-Pr H 2-I CH.sub.3 2-CF.sub.3Ph 251-253 D22 H H
2-Me CH.sub.3 Ph 253-255 D23 Et Et 2-Me CH.sub.3 Ph 182-184 D24
t-Bu H 2-Cl CF.sub.3 Ph 232-234 D25 i-Pr H 2-I CF.sub.3 Ph 271-273
D26 t-Bu H 2-I CF.sub.3 Ph 249-250 D27 i-Pr H 2-Me CH.sub.3 t-Bu
210-211 D28 i-Pr H 2-Br CF.sub.3 Ph 257-259 D29 i-Pr H 2-Br
CH.sub.3 Ph 246-247 D30 i-Pr H 2-Me CF.sub.3 2-pyridinyl 237-238
D31 i-Pr H 2,5-Cl.sub.2 CF.sub.3 Ph >250 D32 B is S, i-Pr H 2-Me
CF.sub.3 Ph 169-172 D33 i-Pr H 2-Me CF.sub.3 2-ClPh 208-209 D34
i-Pr H 2-Cl CF.sub.3 2-ClPh 234-235 D35 i-Pr H 2-Me CF.sub.3 4-ClPh
289-290 D36 i-Pr H 2-Cl CF.sub.3 4-ClPh 276-278 D37 i-Pr H 2-Cl
CF.sub.3 2-pyridinyl 239-240 D38 i-Pr H 2-Me CF.sub.3 2-pyrimidinyl
205-208 D39 i-Pr H 2-Me CF.sub.3 2-(3-CH.sub.3-pyridinyl) 183-187
D40 i-Pr H 2-Me CF.sub.2CF.sub.3 Ph 231-232 D41 i-Pr H 2-Cl
CF.sub.2CF.sub.3 Ph 206-207 D42 t-Bu H 2-Cl CF.sub.2CF.sub.3 Ph
212-213 D43 i-Pr H 2-Br CF.sub.2CF.sub.3 Ph 219-222 D44 i-Pr H 2-Me
CF.sub.3 3-ClPh 278-280 D45 i-Pr H 2-Cl CF.sub.3 3-ClPh 272-273 D46
i-Pr H 2-Me CF.sub.3 2-FPh 217-218 D47 i-Pr H 2-Cl CF.sub.3 2-FPh
220-221 D48 i-Pr H 2-Me CF.sub.3 4-FPh 269-270 D49 i-Pr H 2-Cl
CF.sub.3 4-FPh 279-280 D50 i-Pr H 2-I c-Pr CH.sub.3 222-224 D51
i-Pr H 5-I c-Pr CH.sub.3 215-217 D52 i-Pr H 2-CF.sub.3 CF.sub.3 Ph
247-249 D53 i-Pr H 2-Cl CF.sub.3 i-Pr 255-258 D54 i-Pr H 2-Me
CF.sub.3 3-FPh 277-278 D55 i-Pr H 2-Cl CF.sub.3 3-FPh 256-257 D56
i-Pr H 2-Me CF.sub.3 2-CF.sub.3Ph 215-216 D57 i-Pr H 2-Cl CF.sub.3
2-CF.sub.3Ph 230-231 D58 i-Pr H 2-Me CF.sub.3 2-BrPh 207-208 D59
i-Pr H 2-Cl CF.sub.3 2-BrPh 239-240 D60 i-Pr H 2-OCH.sub.3 CF.sub.3
Ph 215-216 D61 i-Pr H 5-Cl CF.sub.3 2-(3-CH.sub.3-pyridinyl)
224-225 D62 i-Pr H 5-Me CF.sub.3 2-(3-Cl-pyridinyl) 179-181 D63
s-Bu H 2-Cl CF.sub.3 Ph >240 D64 c-Pr H 2-Cl CF.sub.3 Ph >240
D65 Et H 2-Cl CF.sub.3 Ph >240 D66 t-Bu H 2-CF.sub.3 CF.sub.3 Ph
230-233 D67 Et H 2-CF.sub.3 CF.sub.3 Ph 246-249 D68
CH(CH.sub.3)CH.sub.2SCH.sub.3 H 2-CF.sub.3 CF.sub.3 Ph 215-217 D69
CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-CF.sub.3 CF.sub.3 Ph 220-223 D70
i-Pr H 5-Cl CF.sub.3 2-(3-Cl-pyridinyl) 230-233 D71 i-Pr H 5-Me
CF.sub.3 2-thiazolyl 201-203 D72 i-Pr H 5-Me CF.sub.3 2-pyrazinyl
252-253 D73 i-Pr H 5-Me CF.sub.3 4-pyridinyl 224-228 D74 i-Pr H
2-Me CF.sub.3 i-Pr 236-243 D75 i-Pr H 2-Me CF.sub.3 2-CH.sub.3Ph
211-212 D76 i-Pr H 2-Cl CF.sub.3 2-CH.sub.3Ph 232-234 D77 i-Pr H
2-Br CF.sub.3 2-ClPh 247-248 D78 t-Bu H 2-Me CF.sub.3 2-ClPh
216-217 D79 (Ex. 7) i-Pr H 2-Me CF.sub.3 2-(3-CF.sub.3-pyridinyl)
227-230 D80 CH.sub.2CH.sub.2Cl H 2-Cl CF.sub.3 Ph 237-242 D81
CH.sub.2CH.sub.2CH.sub.2Cl H 2-Cl CF.sub.3 Ph 233-239 D82
CH(CH.sub.3)CO.sub.2CH.sub.3 H 2-Cl CF.sub.3 Ph 221-222 D83
S-CH(i-Pr)CO.sub.2CH.sub.3 H 2-Cl CF.sub.3 Ph 212-213 D84 i-Pr H
2-Me CF.sub.3 2,6-Cl.sub.2--Ph 267-268 D85 i-Pr H 2-Cl CF.sub.3
2,6-Cl.sub.2--Ph 286-287 D86 i-Pr H 2-Me Br Ph 253-255 D87 i-Pr H
2-Cl Br Ph 247-248 D88 i-Pr H 2-Me CF.sub.3 i-Bu 205-210 D89 i-Pr H
2-Me CF.sub.3 CH.sub.2Ph 235-237 D90 i-Pr H 2-Me CF.sub.3
2-(3-OCH.sub.3-pyridinyl) 221-222 D91 i-Pr H 2-Me CF.sub.3
3-pyridinyl 260-261 D92 i-Pr H 2-Me CF.sub.3 4-quinolinyl >260
D93 i-Pr H 2-Me CN 2-(3-Cl-pyridinyl) 203-204 D94 i-Pr H 2-Me
CF.sub.3 2,4-F.sub.2--Ph 245-246 D95 i-Pr H 2-Cl CF.sub.3
2,4-F.sub.2--Ph 252-253 D96 i-Pr H 2-Me CF.sub.3 2-Et--Ph 207-209
D97 i-Pr H 2-Cl CF.sub.3 2-Et--Ph 221-222 D98 i-Pr H H CF.sub.3
2-ClPh 206-207 D99 t-Bu H H CF.sub.3 2-ClPh 197-198 D100
CH(CH.sub.3)CH.sub.2OCH.sub.3 H H CF.sub.3 2-ClPh 145-148 D101
CH(CH.sub.3)CH.sub.2SCH.sub.3 H H CF.sub.3 2-ClPh 158-160 D102
CH(CH.sub.3)CH.sub.2SCH.sub.3 H 2-Cl CF.sub.3 Ph 184-186 D103
CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-Cl CF.sub.3 Ph 217-218 D104 n-Pr
H 2-Cl CF.sub.3 Ph 247-248 D105 i-Bu H 2-Cl CF.sub.3 Ph 244-245
D106 CH.sub.3 H 2-Cl CF.sub.3 Ph >250 D107 i-Pr Me 2-Cl CF.sub.3
Ph 193-194 D108 CH.sub.2C.ident.CH H 2-Cl CF.sub.3 Ph >250 D109
CH.sub.2CH.dbd.CH.sub.2 H 2-Cl CF.sub.3 Ph 248-249 D110
CH.sub.2(2-furanyl) H 2-Cl CF.sub.3 Ph 246-247 D111 i-Pr H 2-Me Ph
2-ClPh 133-136 D112 i-Pr H 2-Cl Ph 2-ClPh 220-221 D113 1-Pr H 2-Me
CF.sub.3 4-(3,5-Cl.sub.2-pyridinyl) 239-242 D114 i-Pr H 2-Cl
CF.sub.3 4-(3,5-Cl.sub.2-pyridinyl) 229-231 D115
CH(CH.sub.3)CH.sub.2SCH.sub.3 H 2-Me CF.sub.3 2-ClPh 194-195 D116
CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-Me CF.sub.3 2-ClPh 181-183 D117
s-Bu H 2-Me CF.sub.3 2-ClPh 199-200 D118 c-Pr H 2-Me CF.sub.3
2-ClPh 234-235 D119 n-Pr H 2-Me CF.sub.3 2-ClPh 222-223 D120 i-Bu H
2-Me CF.sub.3 2-ClPh 235-237 D121 Me H 2-Me CF.sub.3 2-ClPh 242-243
D122 i-Pr Me 2-Me CF.sub.3 2-ClPh 90-93 D123 CH.sub.2C.ident.CH H
2-Me CF.sub.3 2-ClPh 215-216 D124 Et H 2-Me CF.sub.3 2-ClPh 228-229
D125 CH.sub.2CH.dbd.CH.sub.2 H 2-Me CF.sub.3 2-ClPh 227-228 D126
CH.sub.2(2-furanyl) H 2-Me CF.sub.3 2-ClPh 218-219 D127
CH(CH.sub.3)CH.sub.2SCH.sub.3 H 2-Me CF.sub.3 Ph 179-180 D128
CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-Me CF.sub.3 Ph 219-220 D129 s-Bu
H 2-Me CF.sub.3 Ph 244-245 D130 c-Pr H 2-Me CF.sub.3 Ph >250
D131 n-Pr H 2-Me CF.sub.3 Ph 238-239 D132 i-Bu H 2-Me CF.sub.3 Ph
237-238 D133 Me H 2-Me CF.sub.3 Ph 263-265 D134 i-Pr Me 2-Me
CF.sub.3 Ph 178-179 D135 CH.sub.2C.ident.CH H 2-Me CF.sub.3 Ph
253-254 D136 Et H 2-Me CF.sub.3 Ph 244-245 D137
CH.sub.2CH.dbd.CH.sub.2 H 2-Me CF.sub.3 Ph 240-241 D138
CH.sub.2(2-furanyl) H 2-Me CF.sub.3 Ph 245-246 D139 i-Pr H
2-OCHF.sub.2 CF.sub.3 2-ClPh 200-201 D140 i-Pr H 2-OCH.sub.3
CF.sub.3 2-ClPh 206-207 D141 i-Pr H 2-I CF.sub.3 2-ClPh 253-256
D142 i-Pr H 2-Me Br 2-ClPh 147-150 D143 i-Pr H 2-Cl Br 2-ClPh
246-247 D144 i-Pr H 2-Me CF.sub.3 2-OCH.sub.3Ph 218-219 D145 i-Pr H
2-Cl CF.sub.3 2-OCH.sub.3Ph 243-244 D146 i-Pr H 2-Me CF.sub.3
1-isoquinolinyl 252-253 D147 CH(CH.sub.3)CH.sub.2SCH.sub.3 H 2-Cl
CF.sub.3 2-ClPh 217-218 D148 CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-Cl
CF.sub.3 2-ClPh 207-208 D149 s-Bu H 2-Cl CF.sub.3 2-ClPh 216-217
D150 c-Pr H 2-Cl CF.sub.3 2-ClPh 261-262 D151 n-Pr H 2-Cl CF.sub.3
2-ClPh 231-232 D152 i-Bu H 2-Cl CF.sub.3 2-ClPh 255-256 D153 Me H
2-Cl CF.sub.3 2-ClPh 233-235 D154 i-Pr Me 2-Cl CF.sub.3 2-ClPh
127-128 D155 CH.sub.2C.ident.CH H 2-Cl CF.sub.3 2-ClPh 226-227 D156
Et H 2-Cl CF.sub.3 2-ClPh 244-246 D157 CH.sub.2CH.dbd.CH.sub.2 H
2-Cl CF.sub.3 2-ClPh 235-236 D158 CH.sub.2(2-furanyl) H 2-Cl
CF.sub.3 2-ClPh 207-208 D159 i-Pr H C.ident.CSi(CH.sub.3).sub.3
CF.sub.3 2-ClPh 256-258 D160 i-Pr H C.ident.CH CF.sub.3 2-ClPh
228-230 D161 i-Pr H 2-Cl C.ident.CH 2-ClPh 219-222 D162 i-Pr H 2-Me
H H, R.sup.7(c) is CH.sub.3 220-223 D163 i-Pr H 2-Me CH.sub.3 Ph,
R.sup.7(c) is Cl 209-210 D164 B is S i-Pr H 2-Cl CF.sub.3 Ph
169-174 D165 i-Pr H 2-Me CF.sub.3 2,6-F.sub.2Ph 223-225 D166 i-Pr H
2-Me CF.sub.3 2-Cl-6-FPh 203-206 D167 i-Pr H 2-Cl CF.sub.3
2-Cl-6-FPh 218-221 D168 i-Pr H 2-Me-4-Br CF.sub.3 2-FPh 232-233
D169 t-Bu H 2-Cl CF.sub.3 2-(3-Cl-pyridinyl) 250-251 D170 65 H 2-Cl
CF.sub.3 2-(3-Cl-pyridinyl) >250 D171 Et Et 2-Cl CF.sub.3 2-ClPh
243-247 D172 Me Me 2-Cl CF.sub.3 2-ClPh 234-235 D173 Et Et 2-Me
CF.sub.3 2-ClPh 237-238 D174 Me Me 2-Me CF.sub.3 2-ClPh 225-226
D175 CH.sub.2CH.sub.2N(Me).sub.2 H 2-Me CF.sub.3 2-ClPh 188-190
D176 i-Pr H 2-Cl CF.sub.3 2-pyrazinyl 242-243 D177 t-Bu H 2-Me-4-Br
CF.sub.3 2-ClPh >260 D178 CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-Me
CF.sub.3 2-(3-Cl-pyridinyl) 176-177 D179 CH(CH.sub.3)CH.sub.2SCH.s-
ub.3 H 2-Me CF.sub.3 2-(3-Cl-pyridinyl) 196-197 D180
CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-Cl CF.sub.3 2-(3-Cl-pyridinyl)
197-198 D181 CH(CH.sub.3)CH.sub.2SCH.sub.3 H 2-Cl CF.sub.3
2-(3-Cl-pyridinyl) 202-203 D182 i-Pr H 2-Me CF.sub.3 2-IPh 221-222
D183 i-Pr H 2-Cl CF.sub.3 2-IPh 238-240 D184 i-Pr H 2-Me CF.sub.3
2-(C.ident.CH)--Ph 215-217 D185 i-Pr H 2-Cl CF.sub.3
2-(C.ident.CH)--Ph 244-246 D186 t-Bu H 2-Cl CF.sub.3
2-(3-Cl-pyridinyl) 250-251 D187 66 H 2-Cl CF.sub.3
2-(3-Cl-pyridinyl) >250 D188 i-Pr H 2-Me CF.sub.3 2-Cl-4-FPh
203-205 D189 i-Pr H 2-Cl CF.sub.3 2-Cl-4-FPh 218-219 D190 Me Me
2-Me CF.sub.3 2-ClPh 225-226 D191 Et Et 2-Me CF.sub.3 2-ClPh
243-247 D192 i-Pr H 2-Me CF.sub.3 2,6-Me.sub.2Ph 259-260 D193 i-Pr
H 2-Cl CF.sub.3 2,6-Me.sub.2Ph 268-269 D194 i-Pr H 2-Me CF.sub.3
2,6-Cl.sub.2-4-CNPh * D195 i-Pr H 2-Me CF.sub.3 2-CNPh 225-235 D196
i-Pr H 2-Me CF.sub.3 2-(OCF.sub.3)Ph 214-215 D197 i-Pr H 2-Cl
CF.sub.3 2-(OCF.sub.3)Ph 223-224 D198 i-Pr H 2-Me CF.sub.3
2-Br-4-FPh 202-203 D199 i-Pr H 2-Cl CF.sub.3 2-Br-4-FPh 222-223
D200 i-Pr H 2-Me CF.sub.3 2-(3-Me-pyrazinyl) 205-207 D201 Me H 2-Cl
CF.sub.3 2-(3-Cl-pyridinyl) 215-220 D202 CH.sub.2C.ident.CH H 2-Cl
CF.sub.3 2-(3-Cl-pyridinyl) 197-198 D203 Me H 2-Me CF.sub.3
2-(3-Cl-pyridinyl) 193-196 D204 Et H 2-Me CF.sub.3
2-(3-Cl-pyridinyl) 204-206 D205 CH.sub.2C.ident.CH H 2-Me CF.sub.3
2-(3-Cl-pyridinyl) 177-178 D206 i-Pr H 2-Me CF.sub.3
4-(8-Cl-quinolinyl) >250 D207 i-Pr H 2-Me CF.sub.3
4-(2-Me-quinolinyl) >250 D208 i-Pr H 2-Cl CF.sub.3
4-(2-Me-quinolinyl) >250 D209 i-Pr H 2-Me CF.sub.3
4-(7-Cl-quinolinyl) >250 D210 i-Pr H 2,4-Br.sub.2 CF.sub.3
2-ClPh 233-234 D211 i-Pr H 2-Br Br 2-ClPh 255-258 D212 Me H 2-Me Br
2-ClPh 236-237 D213 t-Bu H 2-Cl Br 2-ClPh 260-261 D214 Et H 2-Me Br
2-ClPh 254-255 D215 t-Bu H 2-Me Br 2-ClPh 259-260 D216 c-Bu H 2-Cl
CN 2-(3-Cl-pyridinyl) 177-180 D217 i-Pr H 2-Me CF.sub.3
2-(3-Cl-pyridinyl) 237-239 D218 i-Pr H 2-Me CF.sub.3
4-(6-Cl-quinolinyl) >250 D219 Me Me 2-Me CF.sub.3
4-(6-Cl-quinolinyl) >250 D220 O-i-Pr H 2-Cl CF.sub.3 2-ClPh
218-219 D221 i-Pr H 2-Cl CN 2-(3-Cl-pyridinyl) 195-200 D222 t-Bu H
2-Cl CN 2-(3-Cl-pyridinyl) >250 D223 Et H 2-Cl CN
2-(3-Cl-pyridinyl) 200-205 D224 i-Pr H 2-Cl CF.sub.3
2-(3-Me-pyrazinyl) 225-230 D225 t-Bu H 2-Cl CF.sub.3
2-(3-Me-pyrazinyl) 235-240 D226 Et H 2-Cl CF.sub.3
2-(3-Me-pyrazinyl) 210-220 D227 i-Pr H 2-Me CF.sub.3
3-(2-Cl-pyridinyl) * D228 i-Pr H 2-Cl CF.sub.3 2,3-Cl.sub.2Ph
217-219 D229 t-Bu H 2-Cl CF.sub.3 2,3-Cl.sub.2Ph 254-256 D230 i-Pr
H 2-Me CF.sub.3 2,3-Cl.sub.2Ph 208-209 D231 t-Bu H 2-Me CF.sub.3
2,3-Cl.sub.2Ph 232-233 D232 t-Bu H 2-Me-4-Br Br 2-ClPh 239-241 D233
Me H 2-Me-4-Br Br 2-ClPh 150-152 D234 Et H 2-Me-4-Br Br 2-ClPh
223-225 D235 i-Pr H 2-Me-4-Br Br 2-ClPh 197-198 D236 Me H 2-Me
CF.sub.3 2-FPh 245-247 D237 CH.sub.2C.ident.CH H 2-Me CF.sub.3
2-FPh 222-227 D238 O-i-Pr H 2-Cl CN 2-(3-Cl-pyridinyl) 205-206 D239
O-i-Pr H 2-Me CN 2-(3-Cl-pyridinyl) 210-211 D240 Me Me 2-Cl
CF.sub.3 2-ClPh 234-236 D241 CH.sub.2C.ident.CH H 2-Me-4-Br Br
2-ClPh 187-188 *See Index Table Q for .sup.1H NMR data
[0374]
24INDEX TABLE E 67 Com- pound R.sup.2 R.sup.3 (R.sup.4).sub.n
R.sup.7(a) R.sup.7(b) R.sup.7(c) m.p. .degree. C. E1 i-Pr H 2-Me
CH.sub.3 CH.sub.3 H 143-145 E2 i-Pr H 2-Me CH.sub.3
CH.sub.2CF.sub.3 H 198-199 E3 i-Pr H 2-Me CH.sub.3 CH.sub.3 Cl
188-190 E4 i-Pr H 2-Me CH.sub.3 4-CF.sub.3--Ph H 198-199 E5 i-Pr H
2-Me CH.sub.3 2-CF.sub.3--Ph H 211-213 E6 i-Pr H 2-Me CH.sub.3 t-Bu
H 125-127 E7 i-Pr H 2-Me CF.sub.3 CH.sub.2Ph H 130-135 E8 i-Pr H
2-Me H Ph CH.sub.3 249-250 E9 i-Pr H 2-Me H CH.sub.3 Ph 268-270 E10
i-Pr H 2-Cl H Ph CH.sub.3 260-261 E11 i-Pr H 2-Me H
CH.sub.2CF.sub.3 Ph 213-215 E12 i-Pr H 2-Cl H CH.sub.2CF.sub.3 Ph
208-209 E13 i-Pr H 2-Me H CHF.sub.2 Ph * E14 i-Pr H 2-Me CF.sub.3
2-(3-Cl-pyridinyl) H 249-250 *See Index Table Q for .sup.1H NMR
data
[0375]
25INDEX TABLE F 68 Com- pound R.sup.2 R.sup.3 (R.sup.4).sub.n
R.sup.7(a) R.sup.7(b) R.sup.7(c) m.p. .degree. C. F1 i-Pr H 2-Me
CH.sub.2CF.sub.3 CH.sub.3 H 254-255 F2 i-Pr H 2-Me CH.sub.2CF.sub.3
H CH.sub.3 200-205 F3 i-Pr H 2-Me CH.sub.2(3-CF.sub.3)Ph H CH.sub.3
212-215 F4 i-Pr H 2-Cl CH.sub.2CF.sub.3 H CH.sub.3 215-217 F5 i-Pr
H 2-Me Ph H CF.sub.3 223-224 F6 i-Pr H 2-Cl Ph H CF.sub.3 206-208
F7 i-Pr H 2-Me CH.sub.2CF.sub.3 H Ph 156-158 F8 i-Pr H 2-Cl
CH.sub.2CF.sub.3 H Ph 162-164
[0376]
26INDEX TABLE G 69 Compound Q R.sup.2 R.sup.3 (R.sup.4).sub.n
R.sup.7(a) R.sup.7(b) m.p. .degree. C. G1 S i-Pr H 2-Me
4-OCF.sub.3Ph CH.sub.3 233-234 G2 S i-Pr H 2-Me
OCH.sub.2CF.sub.2CF.sub.3 CH.sub.3 170-173 G3 S i-Pr H 2-Me Cl
CH.sub.3 164-167 G4 S i-Pr H 2-Me CH.sub.3 Ph 216-219 G5 S i-Pr H
2-Me C(CH.sub.3).sub.2OH CH.sub.3 * G6 S i-Pr H 2-Me i-Pr CH.sub.3
180-181 G7 S i-Pr H 2-Me i-Pr Ph 182-183 G8 O i-Pr H 2-Me i-Pr
CH.sub.3 163-164 *See Index Table Q for .sup.1H NMR data
[0377]
27INDEX TABLE H 70 Compound Q R.sup.2 R.sup.3 (R.sup.4).sub.n
R.sup.7(a) R.sup.7(b) R.sup.7(c) m.p. .degree. C. H1 S i-Pr H 2-Me
H H H 192-195 H2 S CH(CH.sub.3)CH.sub.2OCH.sub.3 H 2-Me H H H
120-123 H3 S t-Bu H 2-Me H H H 120-123 H4 NMe i-Pr H 2-Me Me H H
193-195 H5 NPh i-Pr H 2-Me H Me H 188-192 H6 NPh i-Pr H 2-Me Br H H
176-179 H7 NPh i-Pr H 2-Me Br H Br 215-216 H8 NPh i-Pr H 2-Me H H
Br 150-154 H9 NPh i-Pr H 2-Me CF.sub.3 H H 182-184 H10 N(2-ClPh)
i-Pr H 2-Me Br H H 100-110 H11 N(2-FPh) i-Pr H 2-Me Br H H 178-179
H12 N(2-FPh) t-Bu H 2-Me Br H H 186-188 H13 N(2-ClPh) t-Bu H 2-Me
Br H H 225-229
[0378]
28INDEX TABLE J 71 Compound R.sup.2 R.sup.3 (R.sup.4).sub.n
R.sup.7(a) R.sup.7(b) m.p. .degree. C. J1 i-Pr H 2-Me Me Me 221-222
J2 i-Pr H H CF.sub.3 Ph 279-281 J3 i-Pr H 2-Me CF.sub.3 Ph 263-268
J4 i-Pr H 2-Cl CF.sub.3 2-ClPh 235-238 J5 i-Pr H 2-Cl CF.sub.3 Ph
245-246 J6 i-Pr H 2-Me CF.sub.3 2-ClPh 240-242 J7 i-Pr H 2-Cl
CF.sub.3 2-F-4-ClPh 246-247 J8 i-Pr H 2-Me CF.sub.3 2-F-4-ClPh
266-268 J9 i-Pr H 2-Me CF.sub.3 2-pyridinyl 258-260
[0379]
29INDEX TABLE K 72 Compound R.sup.2 R.sup.3 (R.sup.4).sub.n
R.sup.7(a) R.sup.7(b) m.p. .degree. C. K1 i-Pr H 2-Me Br H 177-180
K2 t-Bu H 2-Me Br H 188-194
[0380]
30INDEX TABLE L 73 Compound R.sup.2 R.sup.3 (R.sup.4).sub.n
R.sup.7(a) R.sup.7(b) m.p. .degree. C. L1 i-Pr H 2-Me Me Me 203-205
L2 i-Pr H 2-Me Me 2,6-Cl.sub.2Ph 218-223
[0381]
31INDEX TABLE M 74 Compound Q R.sup.2 R.sup.3 (R.sup.4).sub.n
R.sup.7(a) R.sup.7(b) R.sup.7(c) m.p. .degree. C. M1 S i-Pr H 2-Me
Cl Me H 203-205 M2 S i-Pr H 2-Cl Cl Me H 210-213 M3 NCHF.sub.2 t-Bu
H 2-Me H H Ph 165-166 M4 NH i-Pr H 2-Me CF.sub.3 Ph H 118-120 M5
NMe i-Pr H 2-Me CF.sub.3 Ph H 110-112 M6 NCHF.sub.2 i-Pr H 2-Me
2-FPh H H 143-144 M7 NCHF.sub.2 t-Bu H 2-Me 2-FPh H H 120-123 M8
NCH.sub.2CF.sub.3 i-Pr H 2-Me 2-FPh H H 235-237
[0382]
32INDEX TABLE N 75 Compound Het m.p. .degree. C. N1 76 169-171 N2
77 227-230 N3 78 243-246
[0383]
33INDEX TABLE P Compound m.p. .degree. C. P1 79 178-179
[0384]
34 INDEX TABLE Q Compd. No. .sup.1H NMR Data (CDCl.sub.3 solution
unless indicated otherwise).sup.a D194 (DMSO-d6) .delta. 1.03 (d,
6H), 2.18 (s, 3H), 3.92 (m, 1H), 7.22-7.30 (m, 2H), 7.35 (m, 1H),
7.62 (dd, 1H), 7.81 (s, 1H), 8.02 (d, 1H), 8.15 (dd, 1H), 8.55 (dd,
1H), 10.34 (s, 1H). D227 (DMSO-d6) .delta. 1.01 (d, 6H), 2.16 (s,
3H), 3.92 (m, 1H), 7.27 (m, 2H), 7.35 (m, 1H), 7.89 (s, 1H), 7.96
(m, 1H), 8.37 (s, 2H), 10.42 (s, 1H). G5 .delta. 1.22 (d, 6H), 2.05
(s, 6H), 2.31 (s, 3H), 2.76 (s, 3H), 4.18 (m, 1H), 5.94 (d, 1H),
7.20 (dd, 1H), 7.29 (d, 1H), 7.38 (d, 1H), 9.83 (br s, 1H). E13
.delta. 1.12 (d, 6H), 2.32 (s, 1H), 4.14 (m 1H), 4.95 (d, 1H), 7.19
(dd, 1H), 7.28 (t, 1H), 7.32 (m, 5H), 7.59 (dd, 2H), 7.92 (s, 1H),
9.51 (br s, 1H). .sup.a1H NMR data are in ppm downfield from
tetramethylsilane. Couplings are designated by (s)-singlet,
(d)-doublet, (t)-triplet, (q)-quartet, (m)-multiplet, (dd)-doublet
of doublets, (dt)-doublet of triplets, (br s)-broad singlet.
BIOLOGICAL EXAMPLES OF THE INVENTION TEST
[0385] Application: Compounds are formulated in a 10% acetone, 90%
water and 300 ppm X-77 surfactant solution, unless otherwise
indicated. The formulated compounds are applied with a SUJ2
atomizer nozzle with 1/8 JJ custom body (Spraying Systems)
positioned 1/2" above the top of each test unit. There are 6 of
these nozzles that make up the spray boom and this is fixed in a
belt sprayer. A rack (or carrier) of 6 different insect test units
is placed on the conveyor belt and stops so that each unit is
centered under a nozzle. Once the rack is centered, 1 mL of liquid
is sprayed into each test unit; the rack then continues down the
belt to the end of the sprayer to be off-loaded. All experimental
compounds in this screen are sprayed at 250 ppm and replicated
three times.
[0386] Diamondback Moth (DBM)--Plutella Xylostella: The test unit
consists of a small self-contained unit with a 12-14 day old radish
plant inside. These are pre-infested (using a core sampler) with
10-15 neonate larvae on a piece of insect diet. Once 1 mL of
formulated compound has been sprayed into each test unit, the test
units are allowed to dry for 1 hour before a black, screened cap is
placed on the top of the cylinder. They are held for 6 days in a
growth chamber at 25 .degree. C. and 70% relative humidity.
[0387] Plant feeding damage was visually assessed on a scale of
0-10 where 0 is no feeding, 1 is 10% or less feeding, 2 is 20% or
less feeding, 3 is 30% or less feeding through a maximum score of
10 where 10 is 100% of foliage consumed. Of the compounds tested
the following provided excellent levels of plant protection
(ratings of 0-1, 10% or less feeding damage): 1, 2, 3, 4, 6, 7, 9,
10, 13, 14, 15, 19, 20, 24, 27, 28, 29, 30, 31, 32, 33, 35, 37, 38,
39, 51, 52, 53, 60, 61, 62, 63, 64, 65, 66, 68, 69, 72, 73, 74, 75,
76, 79, 80, 84, 86, 88, 89, 90, 92, 96, 97, 98, 99, 100, 101, 102,
103, 107, 113, 124, 126, 127, 143, 144, 146, 147, 148, 150, 151,
152, 153, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 169,
170, 171, 174, 183, 184, 185, 186, 187, 188, 189, 190, 191, 193,
194, 195, 196, 198, 202, 203, 204, 205, 206, 207, 208, 209, 210,
211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 222, 223, 225,
227, 228, 229, 230, 231, 232, 233, 235, 238, 239, 240, 244, 245,
246, 248, 249, 250, 251, 252, 253, 256, 257, 275, 276, 277, 278,
B2, B4, B5, B6, B7, B8, B9, B10, B11, B12, B13, B14, B15, B16, B17,
B18,B19, B20, B21, B23, B24, B25, B28, B29, B30, B31, B32, B33,
B35, B37, B38, B39, B40, B42, B43, B44, B45, B46, B47, B48, B49,
B50, B53, B55, B57, B58, B59, B60, B61, B62, B63, B64, B66, B67,
B68, B69, B70, B71, B72, B74, B75, B76, C1, C2, C3, C4, C5, C7, C8,
C9, C10, C11, C12, C79, D2, D3, D4, D5, D6, D7, D8, D11, D12, D13,
D14, D15, D16, D18, D19, D20, D23, D24, D25, D26, D27, D28, D29,
D30, D32, D33, D34, D37, D38, D39, D40, D41, D42, D45, D46, D47,
D48, D50, D51, D52, D53, D54, D55, D56, D57, D58, D59, D60, D61,
D62, D63, D64, D65, D66, D67, D68, D69, D70, D71, D72, D73, D74,
D75, D76, D77, D78, D79, D81, D83, D84, D85, D86, D87, D88, D89,
D91, D92, D93, D94, D95, D96, D97, D111, D113, D114, D115, D116,
D117, D118, D119, D120, D121, D122, D123, D124, D125, D126, D162,
D164, E4, F2, F5, F6, F7, F8, G2, G3, G5, H1, H2, H3, H4, J3, J4,
J6, M1, M3, N2 and P1.
* * * * *